Sodium Hydroxide → [4-[(4-Fluorophenyl)methoxy]-1-piperidinyl](4-nitrophenyl)methanone

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.6 g of a 50% aqueous sodium hydroxide solution, 10 ml of methylene chloride, 2 g (0.008 mol) of 1-(4-nitrobenzoyl)-4-hydroxypiperidine, 2.32 g (0.012 mol) of 4-fluorobenzyl bromide and 0.15 g (4×10-4 mol) of tetrabutylammonium iodide is stirred for 5 hours at 50° C. After dilution of the reaction medium with 20 ml of water and 30 ml of methylene chloride, the organic phase is decanted, washed with water until the washings are neutral, dried (MgSO4) and evaporated in vacuo. The residual oil obtained crystallises on stirring in diethyl ether. This yields 2.23 g of a product which is purified by dissolving it in 11 ml of dimethylformamide (DMF) and reprecipitating it by the dropwise addition of 11 ml of water, whilst stirring. After washing with water and drying in vacuo, 1-(4-nitrobenzoyl)-4-(4-fluorobenzyloxy)-piperidine, m.p. 120° C., is obtained.

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