IP Library Granted Patent US 7,705,186
Granted Patent B2
US 7,705,186 · App. 11/996,421 · Granted Apr 27, 2010

Process for the preparation of saturated or unsaturated primary fatty amines

Assignee: Novagali Pharma SA
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Quick Facts
Patent No.
US 7,705,186
App. No.
11/996,421
Granted
Apr 27, 2010
Kind
B2
Abstract

Process for the preparation of unsaturated and saturated primary fatty amines comprising the steps of chlorination, treatment by ammonia, reduction and purification.

Claims (12)

1. A process for the preparation of unsaturated and saturated primary fatty amines comprising the steps of:

(a) chlorination of the corresponding acid by treatment with neat thionyl chloride in dichloromethane at reflux temperature, to obtain a solution of the corresponding chloride in dichloromethane,

(b) addition of the chloride solution of step a) to a solution of liquid ammonia in dichloromethane at a temperature comprised between 0 and 10° C. to yield the corresponding amide,

(c) reduction of the amide to amine by treatment with lithium aluminium hydride in tetrahydrofuran, followed by extraction of amine by t-butyl methyl ether,

(d) purification of amine of step c) by treatment in solution in t-butyl methyl ether by hydrochloric acid followed by treatment by acetonitrile to yield amine hydrochloride, and optionally

(e) treatment of amine hydrochloride of step d) by t-butyl methyl ether and a base to yield amine as a free base.

2. The process according to claim 1 , wherein the primary saturated and unsaturated fatty amines are selected from the group consisting of amines comprising 4 to 30 carbon atoms, unsaturated amines being allowed to comprise one or more double bonds, isomers and salts thereof.

3. The process according to claim 1 , wherein the amines are selected from the group consisting of oleylamine, stearylamine and their respective isomers and salts.

4. The process according to claim 1 , wherein the acid used in step a) is oleic acid.

5. The process according to claim 2 , wherein the amines are selected from the group consisting of oleylamine, stearylamine and their respective isomers and salts.

6. The process according to claim 2 , wherein the amines comprise 15 to 24 carbon atoms.

7. The process according to claim 4 , wherein the acid is oleic acid with more than 99% purity.

Assignments (2)
CHANGE OF NAME Recorded Feb 25, 2014
From: NOVAGALI PHARMA SA
To: SANTEN SAS
Reel/Frame 032332/0471 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 3, 2008
From: GIBSON, SCOTT
To: NOVAGALI PHARMA SA
Reel/Frame 021043/0874 →
Priority Claims (1)
EP 05291572 · Jul 22, 2005 · regional
Continuity (1)
Related Publication 20090105504A1 · Apr 23, 2009