Hydrazine → {4-[4-(4-Aminopentyl)phenyl]butyl}carbamic acid benzyl ester

Participants

Reaction Conditions

Reaction Steps

A solution containing compound 25 (0.90 g, 1.81 mmol), hydrazine (0.26 mL, 5.42 mmol) and ethanol (10 mL) was heated at 75° C. for 3 h and then cooled to ambient temperature. The white precipitate was filtered under vacuum and washed with ethanol (3×5 mL). The filtrate and washings were combined and concentrated. The residue was subjected to column chromatography eluting with a mixture of methanol (0-15%), concentrated ammonium hydroxide (0-1.5%) and dichloromethane to afford the desired product 26 (0.59 g, 88%) as a white, waxy solid: 1H NMR (500 MHz, CD3OD) δ 1.08 (d, 3H), 1.36-1.80 (m, 8H), 2.55 (m, 4H), 2.88 (m, 1H), 3.10 (t, 2H), 5.08 (s, 2H), 7.08 (s, 4H), 7.34 (m, 5H); m/z (ESI) 369 [C23H32N2O2+H]+.

Provenance & Evidence