Method for preparation of 1-(2-((2,4-dimethylphenyl)thio)phenyl) piperazine and its salts
AssigneeR L Finechem Private Limited
InventorsVinay Kumar V, Dantham Sowmya, Rajat Rudragoud Biradar Patil, Puttaraju Boregowda, Sivakumar Rallapalli
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Abstract
A method for preparation of 1-(2-((2,4-Dimethylphenyl)thio)phenyl)piperazine and its salts through a novel intermediate, 2-((2,4-dimethylphenyl)thio)-N-hydroxybenzamide involves mild conditions, eco-friendly and cost effective reagents to provide the target compound with purity level greater than 99.5% in high yield.
Claims15
A method of preparation of 1-(2-((2,4-Dimethylphenyl)thio)phenyl) piperazine and its salts, said method comprising acts of—
- a) preparing 2-Mercaptobenzoic acid (2) from 2,2′-disulfanediyldibenzoic acid (1) in a solvent in presence of base and metal catalyst,
- b) coupling 2-Mercaptobenzoic acid (2) with 1-Bromo-2,4-dimethylbenzene (4) to obtain 2-((2,4-dimethylphenyl)thio)benzoic acid (5) in presence of metal catalyst,
- c) reacting 2-((2,4-dimethylphenyl)thio)benzoic acid (5) with halogenating agent and hydroxyl amine hydrochloride to obtain 2-((2,4-dimethylphenyl)thio)-N-hydroxybenzamide (6),
- d) heating 2-((2,4-dimethylphenyl)thio)-N-hydroxybenzamide (6) in presence of base to obtain 2-((2,4-dimethylphenyl)thio) aniline and converting to 2-((2,4-dimethylphenyl)thio) aniline hydrochloride (7),
- e) reacting 2-((2,4-dimethylphenyl)thio) aniline hydrochloride (7) with Bis(2-chloroethyl)amine hydrochloride (8) to obtain 1-(2-((2,4-Dimethylphenyl)thio)phenyl) piperazine hydrochloride (9), and
- f) converting 1-(2-((2,4-Dimethylphenyl)thio)phenyl) piperazine hydrochloride (9) optionally to obtain 1-(2-((2,4-Dimethylphenyl)thio)phenyl) piperazine or its salt.
A compound of formula (6)
A method of preparation of 1-(2-((2,4-Dimethylphenyl)thio)phenyl) piperazine and its salts, said method comprising acts of
- a) heating 2-((2,4-dimethylphenyl)thio)-N-hydroxybenzamide (6) in presence of base in a solvent to obtain 2-((2,4-dimethylphenyl)thio) aniline and converting to 2-((2,4-dimethylphenyl)thio) aniline hydrochloride (7),
- b) reacting 2-((2,4-dimethylphenyl)thio) aniline hydrochloride (7) with Bis(2-chloroethyl)amine hydrochloride (8) in a solvent to obtain 1-(2-((2,4-Dimethylphenyl)thio)phenyl) piperazine hydrochloride (9), and
- c) converting 1-(2-((2,4-Dimethylphenyl)thio)phenyl) piperazine hydrochloride (9) optionally to 1-(2-((2,4-Dimethylphenyl)thio)phenyl) piperazine or its salts.
Dependencies are inferred from the claim text.