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Showing content from https://patents.google.com/patent/ES247829A1/en below:

ES247829A1 - Improvements in or relating to the production of substituted tetrahydro-1,4-oxazines

ES247829A1 - Improvements in or relating to the production of substituted tetrahydro-1,4-oxazines - Google PatentsImprovements in or relating to the production of substituted tetrahydro-1,4-oxazines Info

Publication number: ES247829A1
Authority: ES; Spain
Prior art keywords: benzyl; phenyl; methyl; formic acid; acid
Prior art date: 1958-03-13
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

ES0247829A

Other languages

Spanish (es)

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

CH Boehringer Sohn AG and Co KG

Original Assignee

CH Boehringer Sohn AG and Co KG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1958-03-13

Filing date

1959-03-10

Publication date

1960-03-16

1959-03-10 Application filed by CH Boehringer Sohn AG and Co KG filed Critical CH Boehringer Sohn AG and Co KG

1960-03-16 Publication of ES247829A1 publication Critical patent/ES247829A1/en

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title abstract 2
150000002780 morpholines Chemical class 0.000 title abstract 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 6
-1 5,6,7,8 - tetrahydronaphthyl Chemical group 0.000 abstract 5
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 4
235000019253 formic acid Nutrition 0.000 abstract 4
238000000034 method Methods 0.000 abstract 3
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 abstract 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 abstract 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
125000000217 alkyl group Chemical group 0.000 abstract 2
125000003710 aryl alkyl group Chemical group 0.000 abstract 2
125000003118 aryl group Chemical group 0.000 abstract 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 2
238000006243 chemical reaction Methods 0.000 abstract 2
150000001875 compounds Chemical class 0.000 abstract 2
239000001257 hydrogen Substances 0.000 abstract 2
229910052739 hydrogen Inorganic materials 0.000 abstract 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
150000003839 salts Chemical class 0.000 abstract 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
YBBLOADPFWKNGS-UHFFFAOYSA-N 1,1-dimethylurea Chemical compound CN(C)C(N)=O YBBLOADPFWKNGS-UHFFFAOYSA-N 0.000 abstract 1
150000004896 1,4-oxazines Chemical class 0.000 abstract 1
BHRUEGUXZCYUBO-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-methylmorpholine Chemical compound C1=CC(OC)=CC=C1C1C(C)NCCO1 BHRUEGUXZCYUBO-UHFFFAOYSA-N 0.000 abstract 1
229910015900 BF3 Inorganic materials 0.000 abstract 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract 1
239000002253 acid Substances 0.000 abstract 1
230000002378 acidificating effect Effects 0.000 abstract 1
150000001408 amides Chemical class 0.000 abstract 1
150000001412 amines Chemical class 0.000 abstract 1
239000003054 catalyst Substances 0.000 abstract 1
125000000068 chlorophenyl group Chemical group 0.000 abstract 1
230000032050 esterification Effects 0.000 abstract 1
238000005886 esterification reaction Methods 0.000 abstract 1
238000010438 heat treatment Methods 0.000 abstract 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
125000004464 hydroxyphenyl group Chemical group 0.000 abstract 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
239000002904 solvent Substances 0.000 abstract 1
239000000126 substance Substances 0.000 abstract 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 abstract 1
229960004319 trichloroacetic acid Drugs 0.000 abstract 1
150000003672 ureas Chemical class 0.000 abstract 1
235000005074 zinc chloride Nutrition 0.000 abstract 1
239000011592 zinc chloride Substances 0.000 abstract 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention comprises 2-phenyl-4-benzyl-, 2 - methyl - 3 - phenyl - 4 - benzyl -, 2 - (p - chlorophenyl) - 4 - benzyl -, 2 - phenyl - 3 - benzyl - 4 - methyl -, 2 - (5,6,7,8 - tetrahydronaphthyl - 2) - 3,4 - dimethyl -, and 2 - (m - hydroxyphenyl) - 3 - methyl -, 1,4 - oxazines, 2 - (p - methoxyphenyl) - 3 - methylmorpholine and their acid addition salts. In general tetrahydro-1,4-oxazines of the general formula <FORM:0862198/IV (b)/1> are produced by heating an a -(ethanolamino)-ketone of general formula <FORM:0862198/IV (b)/2> or a salt thereof with formic acid or a compound yielding formic acid under the reaction conditions, R1 being alkyl, aryl or aralkyl and R2, R3, R4 and R5 representing hydrogen or alkyl, aryl or aralkyl residues, and in which R1, R2, R3, R4 and R5 may be the same or different and may be substituted. The process is particularly useful for the production of those compounds in which R1 is a methyl, phenyl, chlorophenyl, methoxyphenyl, hydroxyphenyl or tetrahydronaphthyl radical and R2, R3, R4 and R5 are hydrogen atoms or methyl, phenyl or benzyl radicals. Substances yielding formic acid under the reaction conditions are, for example, formamide or dimethylformamide. The process may be carried out in a solvent medium, e.g. 70-100% aqueous formic acid an amide such as acetamide, dimethylformamide or dimethylacetamide a urea derivative such as N,N1-dimethylurea or an amine such as aniline, dimethylaniline, benzylamine or pyridine. The preferred temperature range for the process is 130-140 DEG C. It is advantageous to add an esterification catalyst such as, for example, perchloric acid, trichloracetic acid, p-toluene sulphonic acid, strongly acidic ion-exchangers, zinc chloride or boron trifluoride. If in the product R3 is a benzyl group or if any of the groups R2, R4 or R5 is a benzyloxy-phenyl residue these may be catalytically hydrogenated to replace the benzyl groups by hydrogen. Specification 791,416 is referred to.

ES0247829A 1958-03-13 1959-03-10 Improvements in or relating to the production of substituted tetrahydro-1,4-oxazines Expired ES247829A1 (en) Applications Claiming Priority (1) Application Number Priority Date Filing Date Title DE862198X 1958-03-13 Publications (1) Publication Number Publication Date ES247829A1 true ES247829A1 (en) 1960-03-16 Family ID=6797453 Family Applications (1) Application Number Title Priority Date Filing Date ES0247829A Expired ES247829A1 (en) 1958-03-13 1959-03-10 Improvements in or relating to the production of substituted tetrahydro-1,4-oxazines Country Status (2) Families Citing this family (2) * Cited by examiner, â Cited by third party Publication number Priority date Publication date Assignee Title WO2011146821A2 (en) 2010-05-21 2011-11-24 Research Triangle Institute 1 - phenylmorpholine derivatives as hydroxybupropion analogues for treating drug dependence ES2687095T3 (en) * 2010-05-21 2018-10-23 Research Triangle Institute Phenylimorpholins and analogues thereof

1959
- 1959-03-10 ES ES0247829A patent/ES247829A1/en not_active Expired
- 1959-03-11 GB GB8413/59A patent/GB862198A/en not_active Expired

Also Published As Similar Documents Publication Publication Date Title ES247829A1 (en) 1960-03-16 Improvements in or relating to the production of substituted tetrahydro-1,4-oxazines US3167561A (en) 1965-01-26 2, 5-diazabicyclo-[2,2,1]heptanes and [2,2,2]octanes GB1111507A (en) 1968-05-01 Substituted amino pyridines GB1024816A (en) 1966-04-06 Basic ethers of substituted hydroxy benzoic acids and process for making same ES2017950B3 (en) 1991-03-16 NEW CHEMICAL PROCEDURE FOR THE OBTAINING OF OXAMIDE DERIVATIVES AND COMPOUNDS OBTAINED THROUGH THE SAME. GB860423A (en) 1961-02-08 Production of compounds of the pyrimidine series US3883532A (en) 1975-05-13 2-Substituted -4,5-diamino-6-cyanopyrimidines US2617808A (en) 1952-11-11 4-thiazolidone-2-n-caproates and preparation thereof US3398155A (en) 1968-08-20 2, 6-dichloro-isonicotinamide derivatives and a method for their preparation US3244723A (en) 1966-04-05 Certain 4-aminothiazole compounds and their preparation US3671535A (en) 1972-06-20 4-imino-oxazolidin-2-ones and process of preparation US3029241A (en) 1962-04-10 Phenylpbperazinylacyl anilines GB1001094A (en) 1965-08-11 Improvements in or relating to the production of n-(3-hydroxy-alkyl)-3,4,5-trimethoxybenzoic acid amides US3291827A (en) 1966-12-13 Process for preparing n, n'-dicyanoamidine salts US4292446A (en) 1981-09-29 Aniline derivatives GB1570591A (en) 1980-07-02 Process for preparing n-methylolated amides and ethers thereof US3247219A (en) 1966-04-19 3'-nitro-2-oxo-3-oxazolidine carboxanilide US2915525A (en) 1959-12-01 Preparation of arylenebenzoxazolols and arylenebenzothiazolols Baumgarten et al. 1967 Reactions of amines. XVI. 1-t-Butyl-3, 3-diphenylaziridinone GB765544A (en) 1957-01-09 Production of amides and ketones having basic substituents GB840361A (en) 1960-07-06 New morpholinoacyl anilides and methods for their preparation Gilligan 1971 Synthesis of N, N-bis (2-fluoro-2, 2-dinitroethyl)-N-alkylamines ATE2528T1 (en) 1983-03-15 PHTHALIDISOCHINOLINE DERIVATIVES, THEIR PRODUCTION AND USE IN PHARMACEUTICALS. GB1367163A (en) 1974-09-18 Boron compounds GB1379428A (en) 1975-01-02 Unsaturated amides containing tertiary amino groups

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