1-Chloro-N,N-2-trimethylpropenylamine → 4-{4-[(4-Cyano-1H-pyrrole-2-carbonyl)-amino]-3-cyclohex-1-enyl-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

A suspension of 101 mg (0.741 mmol) 4-cyano-1H-pyrrole-2-carboxylic acid (Canadian J. Chem. 59: 2673 (1981)) in 20 mL CH3CN was treated with 116 μL (0.741 mmol) (1-chloro-2-methyl-propenyl)-dimethylamine at RT for 20 min. The mixture was added to a solution of 220 mg (0.617 mmol) of 4-(4-amino-3-cyclohex-1-enyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (as prepared in the previous step) in 10 mL CH3CN, stirred at RT for 20 h and the solvents evaporated in vacuo. Silica gel chromatography of the residue on a Varian MegaBond Elut 25-gm column with 10-25% EtOAc-hexane afforded 36.0 mg (12%) of the title compound as an off-white solid: Mass spectrum (ESI, m/z): Calcd. for C24H27N4O3, 419.2 (M−C4H9+2H), found 419.1.

Provenance & Evidence