Dichloromethane → Ammonia dichloromethane

Participants

Reaction Steps

A solution of the product of Example 9 (204 mg), 4-Benzylidene-piperidine (145 mg), and acetic acid (0.05 mL) in DCM (3 mL) was treated with sodium triacetoxyborohydride (300 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (5 mL) and extracted with DCM (3×10 mL). The combined organic phases were dried (magnesium sulfate) and evaporated. Chromatography of the residue (1 to 5% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (308 mg). 1H NMR (400 MHz, CDCl3): 7.30 (m, 2H), 7.24–7.16 (m, 4H), 6.84 (m, 2H), 6.26 (s,1H), 3.99 (t, J=6.3 Hz, 2H), 3.46 (s, 2H), 2.54–2.44 (m, 6H), 2.43–2.35 (m, 6H), 1.97 (m, 2H), 1.74 (br, 1H), 1.63–1.56 (m, 4H), 1.47–1.40 (m, 2H).

Provenance & Evidence