Dichloromethane → Ammonia dichloromethane

Participants

Reaction Steps

A solution of 2-(3-piperidin-1-yl-propoxy)-benzaldehyde (269 mg), 2-aminopyridine (110 mg), and acetic acid (0.07 mL) in DCM (5 mL) was treated with sodium triacetoxyborohydride (410 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 (128 mg). 1H NMR (400 MHz, CDCl3): 8.07 (m, 1H), 7.37 (m, 1H), 7.29 (m, 1H), 7.22 (m, 1H), 6.91–6.84 (m, 2H), 6.54 (m, 1H), 6.37 (m, 1H), 5.00 (m, 1H), 4.48 (d, J=5.6, 2H), 4.04 (t, J=6.3 Hz, 2H), 2.52 (m, 2H), 2.41 (br, 4H), 2.02 (m, 2H), 1.64–1.57 (m, 4H), 1.47–1.40 (m, 2H).

Provenance & Evidence