5-Chlorovaleryl chloride → N-(Benzyloxy)-N-(4-cyanobutyl)-5-chloropentanamide

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Reaction Conditions

Reaction Steps

A solution of 5-chlorovaleryl chloride (3.66 g, 23.6 mmol) in CH2Cl2 (50 mL) was slowly dripped into a mixture of amine 2 (n=4) (4.08 g, 20.0 mmol) in CH2Cl2 (100 mL) and 1N NaOH (200 mL) which had been cooled to 0° C. The mixture was stirred at 0° C. for 30 minutes and at room temperature overnight. The layers were separated and the aqueous layer was further extracted with CH2Cl2 (2×150 mL). The combined organic extracts were washed with saturated sodium chloride, and solvent was removed in vacuo. The crude oil was passed through a short silica gel column, eluting with EtOAc, to give 6.0 g (93%) of (3) as an oil; NMR δ 1.57-1.97 (m, 8 H), 2.35 (t, 2 H, J=6), 2.40 (t, 2 H, J= 6), 3.50 (t, 2 H, J=6), 3.67 (t, 2 H, J=6), 4.80 (s, 2 H), 7.37 (s, 5 H). Anal. (C17H23ClN2O2) C, H, N.

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