Piperidine → HCID 178484018, compound

Participants

Reaction Steps

A solution of 222 mg (corresponds to 0.40 mmol) of crude trans-methanesulfonic acid 3-(4-{[(4-chloro-phenoxycarbonyl)-methyl-amino]-methyl}-cyclohexyl)-prop-2-ynyl ester in 4 ml of methanol was cooled to 0° C., treated with 0.34 ml (4 mmol) of piperidine and stirred over night at room temperature. The solvent was evaporated and the residue extracted with aqueous saturated NaHCO3/ether (3×). The organic phase was dried with sodium sulfate, filtered and evaporated. Purification by flash column chromatography on silica gel (methylenechloride/methanol 99:1 to 98:2) gave 92 mg (57%) of pure trans-methyl-[4-(3-piperidin-1-yl-prop-1-ynyl)-cyclohexylmethyl]-carbamic acid 4-chloro-phenyl ester as light yellow viscous oil, MS: 403 (MH+, 1Cl). The following compounds were prepared from the corresponding mesylates and secondary amines:

Provenance & Evidence