1-Chloroethyl chloroformate → HCID 58860729, compound

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Reaction Steps

Dissolve (S)-1,4-dibenzyl-2-[2-(3-chloro-phenyl)-ethyl]-piperazine (4.48 g, 11.07 mmol) in dichloroethane (40 ml). Cool the solution to 0° and then add 1-chloroethyl chloroformate (4.75 g, 33.21 mmol) dropwise. Warm the solution to ambient temperature and then heat it at reflux for 42 hours. Remove the dichloroethane under vacuum and reflux the resulting residue in methanol (100 ml) for 1 hour. Remove the methanol under vacuum and dissolve the resulting precipitate in 1N NaOH. Extract the aqueous layer with dichloromethane and then combine, wash (brine), dry (sodium sulfate), and reduce the extracts to residue. Purify the residue on silica gel using dichloromethane/2N ammonia in methanol (90:10) to give 407.6 mg (16%) of the title compound: mp 93°–97°; mass spectrum (ion spray): m/z=225.3 (M+1).

Provenance & Evidence