1-Chloroethyl chloroformate → HCID 69071710, compound

Participants

Reaction Steps

Combine N-[3-(1-benzyl-3-methyl-piperidin-4-yloxy)-phenyl]-2-chloro-4-fluoro-benzamide cis isomer 1 (preparation 80, 0.52 g, 1.15 mmol), 1,2-dichloroethane (20 mL) and 1-chloroethyl chloroformate (1.24 mL, 11.5 mmol), stir and heat at reflux. After 2 hr., cool to ambient temperature and concentrate. Dissolve the residue in methanol (20 mL), stir and heat at reflux. After 1.5 hr., cool to ambient temperature. Load reaction mixture on an SCX column (10 g), wash with methanol, elute with 2M ammonia/methanol. Concentrate eluent. Purify residue by silica gel flash chromatography eluting with 10% (2M NH3/methanol)/methylene dichloride and converted to the mono hydrogen chloride salt to obtain the title compound (0.139 g, 33%). Mass spectrum: obs. m/z 363.1292; calc. m/z 363.1275; Analysis calculated for C19H21Cl2FN2O2.0.35H2O: C, 56.39; H, 5.38; N, 6.92. Found: C, 56.43; H, 5.48; N, 6.73.

Provenance & Evidence