Benzaldehyde → 1-Benzyl-hexahydro-4H-azepin-4-one

Participants

Reaction Steps

(may be prepared as described in Synthetic Communications (1992), 22(9), 1249-58) was suspended in dichloromethane (100 ml) and triethylamine (9.31 ml, 66.9 mmol) added, followed by benzaldehyde (68 ml, 0.669 mol). The mixture was stirred at room temperature for 30 minutes under argon, then cooled in ice whilst sodium triacetoxyborohydride (17 g, 80 mmol) was added portionwise. The mixture was stirred and allowed to reach room temperature, then stirred for 2 hours. 2M sodium hydroxide solution (80 ml) was added, the layers separated and the aqueous layer extracted with dichloromethane (×2). The combined organic extracts were evaporated to half volume, then extracted with 2M hydrochloric acid (2×100 ml). The aqueous layer was made basic with 50% sodium hydroxide solution and extracted with dichloromethane (×2). The combined organic extracts were dried over magnesium sulphate and evaporated to afford the title compound (D2). 1H NMR (CDCl3) δ 1.82-1.88 (2H, m), 2.52-2.55 (2H, m), 2.59-2.62 (2H, m) 2.71-2.76 (4H, m) 3.65 (1H, s) 7.23-7.33 (5H, m).

Provenance & Evidence