Dichloromethane → Ammonia dichloromethane

Participants

Reaction Steps

A solution of the product of Example 9 (215 mg), 1-(3-phenyl-allyl)-piperazine (176 mg), and acetic acid (0.06 mL) in DCM (3 mL) was treated with sodium triacetoxyborohydride (290 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 (sodium sulfate) and evaporated. Chromatography of the residue (1–5% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (303 mg). 1H NMR (400 MHz, CDCl3): 7.36 (m, 2H), 7.30 (m, 2H), 7.24–7.18 (m, 3H), 6.83 (d, J=8.6 Hz, 2H), 6.51 (d, J=15.9 Hz, 1H), 6.31–6.23 (m, 1H), 3.98 (t, J=6.3 Hz, 2H), 3.45 (s, 2H), 3.15 (m, 2H), 2.60–2.32 (m, 12H), 1.67 (br, 1H), 1.62–1.56 (m, 4H), 1.47–1.40 (m, 2H).

Provenance & Evidence