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GB1413070A - Process for the production of - norfenfluramine and - fenfluramine and salts thereof

Publication number

GB1413070A

GB1413070A GB3592373A GB3592373A GB1413070A GB 1413070 A GB1413070 A GB 1413070A GB 3592373 A GB3592373 A GB 3592373A GB 3592373 A GB3592373 A GB 3592373A GB 1413070 A GB1413070 A GB 1413070A

Authority

GB

United Kingdom

Prior art keywords

norfenfluramine

prepared

group

salt

formula

Prior art date

1973-07-27

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

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• 150000003839 salts Chemical class 0.000 title abstract 4
• 229960001582 fenfluramine Drugs 0.000 title 1
• MLBHFBKZUPLWBD-SSDOTTSWSA-N (2R)-1-[3-(trifluoromethyl)phenyl]-2-propanamine Chemical compound C[C@@H](N)CC1=CC=CC(C(F)(F)F)=C1 MLBHFBKZUPLWBD-SSDOTTSWSA-N 0.000 abstract 4
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
• 229910052799 carbon Inorganic materials 0.000 abstract 2
• 125000004432 carbon atom Chemical group C* 0.000 abstract 2
• 150000001875 compounds Chemical class 0.000 abstract 2
• RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 abstract 1
• DBGIVFWFUFKIQN-SECBINFHSA-N Levofenfluramine Chemical compound CCN[C@H](C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-SECBINFHSA-N 0.000 abstract 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
• 230000021736 acetylation Effects 0.000 abstract 1
• 238000006640 acetylation reaction Methods 0.000 abstract 1
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
• 238000005984 hydrogenation reaction 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
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
  • C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
  • C07C209/52—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of imines or imino-ethers
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
  • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
  • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
  • C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
  • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
  • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
  • C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups

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

1413070 (-)-Norfenfluramine BEECHAM GROUP Ltd 18 July 1974 [27 July 1973] 35923/73 Heading C2C (-)-Norfenfluramine or a salt thereof may be prepared by hydrogenating the novel compound of Formula (I) or a salt thereof: where R is a phenyl group, optionally substituted in the meta- or para-positions by a non- reactive group that does not interfere with the hydrogenation, the carbon atom marked with one asterisk has the same configuration as (-)-norfenfluramine and the carbon atom marked with two asterisks has the configuration found in (+ )-a-methylbenzylamine. The compound of Formula (I) may be prepared by reducing a compound of Formula II or a salt thereof: which may itself be prepared by reacting l-(mtrifluoromethylphenyl)propan-2-one with (+ )- α-methylbenzylamine. (-)-Fenfluramine may be prepared by the acetylation of (-)-norfenfluramine in conventional manner followed by reduction of the acetyl group to an ethyl group.

• 1973
  • 1973-07-27 GB GB3592373A patent/GB1413070A/en not_active Expired

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