Triethylamine → Hydrochloric Acid

Participants

Reaction Steps

To a stirred solution of 3-bromopropanol (5.56 g, 0.04 mol) in 50 mL of methylene chloride, adamantane-1-carboxylic acid chloride (5.6 g, 0.02 mol) and triethylamine (4 g, 0.04 mol) were added. The reaction mixture was stirred at room temperature overnight, the methylene chloride was washed with water, dried over anhydrous Na2SO4 and removed under reduced pressure to afford 12 g of the intermediate adamantane-1-carboxylic acid bromopropyl ester. The title compound was prepared by stirring 4-(3-chlorophenyl)-1-piperazine (2.7 g, 0.011 mol), adamantane-1-carboxylic acid bromopropyl ester (3.5 g, 0.011 mol) and triethylamine (2.5 g, 0.025 mol) in 50 mL of CH2Cl2 for 24 hours. The methylene chloride was washed with water, dried (anhydrous Na2SO4) and removed under reduced pressure. The remaining residue was subjected to preparative HPLC over silica gel using ethylacetate as the eluent and the desired product (TLC Rf =0.6 in 30% methanol/ethylacetate) was separated and converted to the dihydrochloride salt with ethanolic HCl (1 g, 20% yield), mp. 220°-222° C.

Provenance & Evidence