Sodium hydride → HCID 20517738, compound

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Reaction Steps

A mixture of 31.3 g 5-chloro-2-fluoro-N-(1-methyl-4-piperidinyl)-benzamide, 5.6 g of 55% sodium hydride/oil dispersion and 250 ml dimethylformamide are stirred at 45° for 40 minutes. Thereafter 29.7 g 2-fluoro-nitrobenzene are added and stirring is continued at 50° for 80 hours. The solvent is evaporated in vacuo and the residue partitioned between 2 N hydrochloric acid and toluene. The acid phase is made alkaline with 2 N sodium hydroxide and extracted with methylene chloride. The organic phase is dried and evaporated in vacuo to give the heading compound, which recrystallised from ether has a m.p. 164°-166°.

Provenance & Evidence