Process for preparation of an antidepressant compound
AssigneeSun Phamaceuutical Industries Ltd.
InventorsKartik Patel, Nischal Patel, Rajeev Rehani, Rajamannar Thennati
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Abstract
The present invention provides optically pure (S)-(+)-N-methyl-3-(1-naphthaleneoxy)-3-(2-thienyl)propanamine, a compound of formula (I), and optically pure (S)-isomer of compound of formula 4, wherein R1 and R2 both are methyl or R1 is methyl and R2 is benzyl or substituted benzyl group and process for preparation thereof. Formula (I) and (IV). In another aspect the present invention provides a process for preparation of an acid addition salt of compound of formula (I).
Claims15
A process for preparation of (S)-isomer of compound of formula 4,
- wherein R1 and R2 both are methyl or R1 is methyl and R2 is benzyl or substituted benzyl group, comprising the steps of
- a) reacting a mixture of R and S enantiomers of compound of formula 4 with Di-para-toluoyl-L-tartaric acid to precipitate the salt of (S)-isomer of the compound of formula 4 with Di-para-toluoyl-L-tartaric acid;
- and
- b) converting the said precipitated salt to the (S)-isomer of the compound of formula 4.
A process for preparation of an acid addition salt of (S)-(+)-N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, a compound of formula 1A,
- comprising reacting a compound of formula 1 in the form of free base with a compound represented by formula BHX in a protic solvent, wherein B represents a base and HX represents an acid.
A process for preparation of (±)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, comprising racemization of (R)—N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine by treatment with a base.
(S)-(+)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine with greater than 98% enantiomeric excess.
Crude (S)-(+)-N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl) propanamine hydrochloride with greater than 99% enantiomeric excess.
Dependencies are inferred from the claim text.