4-methylidenepiperidine;hydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of 4-methylene-piperidine hydrochloride (1.00 g, 8.12 mmol, JOC 66,2487-2492,2001) in 10 mL anhydrous dichloromethane at room temperature is added 2,4-dimethoxybenzoyl chloride (1.63 g, 8.12 mmol) and TEA (4 g, 40 mmol). The reaction mixture is allowed to stir for 16 hours. Dichloromethane is removed in vacuo, and the resultant residue is purified through silica gel chromatography (95% DCM, 5% MeOH) to give (2,4-dimethoxy-phenyl)-(4-methylene-piperidin-1-yl)-methanone. Yield: 1.62 g, 6.23 mmol. m/z (MS) M+1 261.01. Dichloromethane is removed in vacuo the resultant residue is purified through silica gel chromatography (95% DCM, 5% MeOH)