1-Chloroethyl chloroformate → HCID 10353664, compound

Participants

Reaction Steps

To a solution of 3-methyl-2,3,4,5,10,11-hexahydro-1H,9H-cyclopenta[b][1,4]diazocino[7,8,1-hi]indole (90 mg, 0.36 mmole) in dichloroethane (10 mL) was added 1-chloroethyl chloroformate (0.15 mL, 1.3 mmole) and the solution refluxed for 24 hours under nitrogen. The reaction mixture was cooled to room temperature and the solvent removed in vacuo and replaced with methanol (25 mL) and refluxed for another 3 hours under nitrogen. The solvent was removed in vacuo and the residue purified by flash column chromatography (silica gel, 1.5% methanol in dichloromethane) to provide 27 mg of the title compound as a light yellow oil. The oil was further treated with one equivalent of fumaric acid in ethanol to form a fumarate salt, mp 180-183° C., which contained a slight excess of fumaric acid. MS (ESI) m/z 227 ([M+H]+).

Provenance & Evidence