1,2-Dichloroethane → N-[2-[4-(4-Indolyl)-1-piperazinyl]ethyl]-N-(2-pyridyl)cyclohexanecarboxamide HCL

Participants

Reaction Steps

A mixture of 0.94 g of N-formylmethyl-N-(2-pyridyl)cyclohexanecarboxamide, 0.69 g of 1-(4-indolyl)piperazine, 1.21 g of sodium triacetoxyborohydride, 0.44 ml of acetic acid and 30 ml of 1,2-dichloroethane was stirred at room temperature for 3 h. Afterwards, it was diluted with 20 ml of water and alkalinized to pH=10 with 20% Na2CO3. The aqueous layer was extracted twice with 1,2-dichloroethane and the combined organic layers were dried (sodium sulfate) and evaporated to dryness in vacuo affording a crude which was purified by flash chromatography (methylene chloride-methanol 98:2 to 95:5) affording 0.96 g of the title compound as a base. This was dissolved in 40 ml of methylene chloride and to the solution was added 3.8 N hydrogen chloride in diethyl ether. The precipitated title compound was filtered, yielding 0.66 g. M.p. 181-7° C.

Provenance & Evidence