Norchlorcyclizine → HCID 22161647, compound

Participants

Reaction Steps

A mixture of 1.53 g of 1-(chloroacetyl)-1,2-dihydro-4-[3-(trifluoromethyl)phenyl]imidazo[1,5-a]pyrimidine-8-carbonitrile, 1.32 g of N-(p-chlorobenzhydryl)piperazine and 990 mg of [1,8-bis(dimethylamino)naphthalene, N,N,N',N'-tetramethyl-1,8-naphthalenediamine] in 60 ml of toluene was stirred and heated at reflux for 17 hours. The reaction mixture was filtered hot. The filtrate was cooled, then shaken with 50.0 ml of 1N sodium hydroxide and worked up by the procedure of Example 7 to obtain a viscous oil. The oil in ethyl acetate was passed through a silica column to give a solid upon evaporation of the solvent. The solid was dissolved in 40% ethyl acetate/hexane and again passed through a short silica column. Evaporation of the solvent in vacuo gave 2.00 g of the desired product as a yellow solid, mp 105°-107° C.

Provenance & Evidence