Hydrogen Bromide → Norchlorcyclizine

Participants

Reaction Conditions

Reaction Steps

Levorotatory (−)-1-[(4-chlorophenyl)phenylmethyl]-4-[(phenyl)sulfonyl]piperazine (100 gm) is added to 30% hydrobromic acid in acetic acid (271 ml). The suspension is stirred at 25-30° C. for 1 hour, heated to 60° C. and maintained for 4 hours. Water (1000 ml) is added to reaction mass and cooled to 25-30° C. The precipitate formed is filtered off and washed with water (250 ml). Toluene (500 ml) is added to the aqueous layer and basified with 50% aqueous solution of sodium hydroxide. Toluene layer is separated, distilled under reduced pressure and the residue left is recrystallised from boiling hexane (160 ml). The solution is filtered and allowed to recrystallise first at ambient temperature, and then in an ice bath. The product is filtered off, washed with hexane and dried to obtain 55 gm of levorotatory (−)-1-[(4-chloro phenyl)phenylmethyl]piperazine [M.R: 89-93° C.; [α]D25=−15.6 (c=1, methanol); Chiral Purity by HPLC: 99.7%].

Provenance & Evidence