4-chloro-N-methylpiperidine → HCID 57535470, compound

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of Mg turnings (3.82 g, 157 mmol) in dry THF, under N2, was treated with 2-3 drops of dibromoethane, followed by slow addition of freshly-distilled 4-chloro-N-methylpiperidine (7.00 g, 52.4 mmol) in THF. The reaction mixture was heated at 70° C. for 3 h, cooled to room temperature, added to 2-fluoro-5-iodobenzoyl chloride (10.1 g, 35.6 mmol) in THF at −78° C., warmed to room temperature over 1 h and concentrated in vacuo. The resultant residue was dissolved in EtOAc, washed with brine, dried over Na2SO4 concentrated in vacuo. This residue was purified by chromatography (0-10% CH2Cl2 in CH3OH as eluent) to provide the title compound (6.50 g, 53%), characterized by HNMR and mass spectral analyses.

Provenance & Evidence