Dichloromethane → Ammonia dichloromethane

Participants

Reaction Steps

A solution of 2-(3-piperidin-1-yl-propoxy)-benzaldehyde (212 mg), 4-benzylidene-piperidine (154 mg), and acetic acid (0.05 mL) in DCM (3 mL) was treated with sodium triacetoxyborohydride (290 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (6 mL) and extracted with DCM (3×10 mL). The combined organic phases were dried (sodium sulfate) and evaporated. Chromatography of the residue (1–5% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (148 mg). 1H NMR (400 MHz, CDCl3): 7.37 (m, 1H), 7.30 (m, 2H), 7.23–7.16 (m, 4H), 6.92 (m, 1H), 6.86 (m, 1H), 6.27 (s, 1H), 4.00 (t, J=6.3 Hz, 2H), 3.60 (s, 2H), 2.60 (m, 2H), 2.55–2.46 (m, 6H), 2.44–2.37 (m, 6H), 2.00 (m, 2H), 1.64–1.56 (m, 4H), 1.47–1.40 (m, 2H).

Provenance & Evidence