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GB883220A - Improvements in or relating to morpholine derivatives

GB883220A - Improvements in or relating to morpholine derivatives - Google PatentsImprovements in or relating to morpholine derivatives Info

Publication number: GB883220A
Authority: GB; United Kingdom
Prior art keywords: general formula; acid addition; morpholine; dextrorotatory; diethanolamine
Prior art date: 1959-06-26
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

GB2210859A

Inventor

Hans C Stark

Harm Siemer

Adolf Doppstatt

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.)

Ravensberg GmbH Chemische Fabrik

Original Assignee

Ravensberg GmbH Chemische Fabrik

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.)

1959-06-26

Filing date

1959-06-26

Publication date

1961-11-29

1959-06-26 Application filed by Ravensberg GmbH Chemische Fabrik filed Critical Ravensberg GmbH Chemische Fabrik

1959-06-26 Priority to GB2210859A priority Critical patent/GB883220A/en

1961-11-29 Publication of GB883220A publication Critical patent/GB883220A/en

Status Expired legal-status Critical Current

Links

150000002780 morpholines Chemical class 0.000 title abstract 4
150000003839 salts Chemical class 0.000 abstract 4
239000002253 acid Substances 0.000 abstract 3
125000000217 alkyl group Chemical group 0.000 abstract 3
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 2
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 abstract 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
229910015900 BF3 Inorganic materials 0.000 abstract 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
230000002152 alkylating effect Effects 0.000 abstract 1
150000001450 anions Chemical class 0.000 abstract 1
238000009835 boiling Methods 0.000 abstract 1
150000001875 compounds Chemical class 0.000 abstract 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
239000012024 dehydrating agentsâ Substances 0.000 abstract 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 abstract 1
238000010438 heat treatment Methods 0.000 abstract 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
238000002955 isolation Methods 0.000 abstract 1
229940101209 mercuric oxide Drugs 0.000 abstract 1
238000000034 method Methods 0.000 abstract 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 1
238000002360 preparation method Methods 0.000 abstract 1
239000007858 starting material Substances 0.000 abstract 1
125000001424 substituent group Chemical group 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
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises dextrorotatory morpholine derivatives of the general formula <FORM:0883220/IV (b)/1> and their acid addition salts containing pharmaceutically acceptable anions wherein R is a cyclohexyl or a phenyl group, R1 is a C1-5 alkyl R2 is a hydrogen atom or a C1-5 alkyl group, and the substituents R1 and R2 are in threo configuration with respect to one another, and a process for the preparation of both racemic and optically active morpholines of above general formula by heating an acid addition salt of a racemic or optically active diethanolamine of the general formula <FORM:0883220/IV (b)/2> with zinc chloride and separating from the reaction mass the morpholine derivative formed or an acid addition salt thereof. A small quantity of phosphorus pentoxide may be used as an auxiliary dehydrating agent. A laevorotatory diethanolamine is cyclised to form a dextrorotatory morpholine. The diethanolamines above, used as starting materials, are prepared by adding R.CH(OH).C:H to boron trifluoride containing red mercuric oxide to form the corresponding 1,4-dioxane of the formula <FORM:0883220/IV (b)/3> opening the ring, without isolation of the compound, by boiling with hydrochloric acid, hydrogenating the ketol and aminating it with a salt of an aminoalcohol H2NCH2CH2COH) and where R2 is an alkyl group, alkylating the product so obtained. Specification 773,780, U.S.A. Specifications Re-issue 615,488 and 2,835,669, and German Specifications 95,854 and 844,006 are referred to.

GB2210859A 1959-06-26 1959-06-26 Improvements in or relating to morpholine derivatives Expired GB883220A (en) Priority Applications (1) Application Number Priority Date Filing Date Title GB2210859A GB883220A (en) 1959-06-26 1959-06-26 Improvements in or relating to morpholine derivatives Applications Claiming Priority (1) Application Number Priority Date Filing Date Title GB2210859A GB883220A (en) 1959-06-26 1959-06-26 Improvements in or relating to morpholine derivatives Publications (1) Publication Number Publication Date GB883220A true GB883220A (en) 1961-11-29 Family ID=10174026 Family Applications (1) Application Number Title Priority Date Filing Date GB2210859A Expired GB883220A (en) 1959-06-26 1959-06-26 Improvements in or relating to morpholine derivatives Country Status (1) Cited By (4) * Cited by examiner, â Cited by third party Publication number Priority date Publication date Assignee Title FR2325647A1 (en) * 1975-09-27 1977-04-22 Basf Ag PROCESS FOR PREPARING N-SUBSTITUTED TETRAHYDRO-1,4-OXAZINES EP0094565A3 (en) * 1982-05-13 1984-01-11 Basf Aktiengesellschaft Process for the preparation of cis-2,6-dimethyl morpholine WO2011146850A1 (en) * 2010-05-21 2011-11-24 Research Triangle Institute Phenylmorpholines and analogues thereof US8906908B2 (en) 2010-05-21 2014-12-09 Research Triangle Institute Hydroxybupropion analogues for treating drug dependence

1959
- 1959-06-26 GB GB2210859A patent/GB883220A/en not_active Expired

Cited By (6) * Cited by examiner, â Cited by third party Publication number Priority date Publication date Assignee Title FR2325647A1 (en) * 1975-09-27 1977-04-22 Basf Ag PROCESS FOR PREPARING N-SUBSTITUTED TETRAHYDRO-1,4-OXAZINES EP0094565A3 (en) * 1982-05-13 1984-01-11 Basf Aktiengesellschaft Process for the preparation of cis-2,6-dimethyl morpholine WO2011146850A1 (en) * 2010-05-21 2011-11-24 Research Triangle Institute Phenylmorpholines and analogues thereof US8906908B2 (en) 2010-05-21 2014-12-09 Research Triangle Institute Hydroxybupropion analogues for treating drug dependence US9527823B2 (en) 2010-05-21 2016-12-27 Research Triangle Institute Hydroxybupropion analogues for treating drug dependence US9617229B2 (en) 2010-05-21 2017-04-11 Research Triangle Institute Phenylmorpholines and analogues thereof Similar Documents Publication Publication Date Title ES383503A1 (en) 1973-04-16 1,1,1-trichloro-2-amido-2-amino-ethanes GB913866A (en) 1962-12-28 Improvements in or relating to amino-norcamphane compounds GB883220A (en) 1961-11-29 Improvements in or relating to morpholine derivatives GB1090304A (en) 1967-11-08 Novel phenanthridine derivatives and a process for the manufacture thereof ES448629A1 (en) 1977-07-01 Benzoxazole derivatives, process for their preparation and their use as optical brighteners GB1061571A (en) 1967-03-15 N,n'-disubstituted piperazines and process for their manufacture GB959203A (en) 1964-05-27 Indole derivatives and salts thereof GB869978A (en) 1961-06-07 Method of producing n-alkyl-and-cycloalkyl-piperidine carboxylic acid amides GB894049A (en) 1962-04-18 Method of preparing 10-(1-substituted-3-pyrrolidylmethyl) phenothiazines GB1064132A (en) 1967-04-05 New quinoline derivatives, process for their production and use thereof in the production of carbostyril derivatives GB843908A (en) 1960-08-10 Novel morphinan derivatives and the manufacture thereof GB907528A (en) 1962-10-03 Substituted furfurylamines and tetrahydrofurfurylamines GB1017450A (en) 1966-01-19 2-amino-4-alkoxy-ÃºÃ-triazines GB1042191A (en) 1966-09-14 Process for the preparation of hydroxylamine derivatives GB1105007A (en) 1968-03-06 Nitrone derivatives and processes for preparation thereof GB1120310A (en) 1968-07-17 Substituted naphthotriazines ES432465A1 (en) 1976-11-16 Substituted 4-biphenylyl-butenoic acids esters and amides and pharmaceutical compositions containing them GB702847A (en) 1954-01-27 Process for the preparation of thienyl substituted tertiary amines GB827832A (en) 1960-02-10 Improvements in or relating to substituted amines GB873781A (en) 1961-07-26 Novel sulphanilamido-pyrimidines and acid addition salts thereof and a process for the manufacture of same GB932016A (en) 1963-07-24 Process for the preparation of boric phenthiazines GB1004927A (en) 1965-09-22 Improvements in or relating to amino-ketones, their preparation and compositions containing them GB829728A (en) 1960-03-09 Acridinyl-10-oxides GB904680A (en) 1962-08-29 Process for the production of o-quinones GB1019462A (en) 1966-02-09 Improvements in or relating to novel 3-azabicyclo-[3.2.2]-nonane derivatives

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