Dichloromethane → Ammonia dichloromethane

Participants

Reaction Steps

A solution of the product of Example 9 (227 mg), methyl-(1-methyl-piperidin-4-yl)-amine (118 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 (270 mg). 1H NMR (400 MHz, CDCl3): 7.19 (d, J=8.6 Hz, 2H), 6.83 (d, J=8.6 Hz, 2H), 3.98 (t, J=6.3 Hz, 2H), 3.49 (s, 2H), 2.90 (m, 2H), 2.78 (m, 2H), 2.46 (m, 2H), 2.43–2.35 (m, 4H), 2.26 (s, 3H), 2.17 (s, 3H), 2.00–1.87 (m, 5H), 1.78 (m, 2H), 1.68 (m, 2H), 1.61–1.54 (m, 4H), 1.47–1.40 (m, 2H).

Provenance & Evidence