1,2-Dichloroethane → Ammonia dichloromethane

Participants

Reaction Steps

A solution of the product of Example 9 (175 mg), dimethylamine hydrochloride (64 mg), and acetic acid (0.05 mL) in DCE (3 mL) was treated with sodium triacetoxyborohydride (210 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (1 mL) and extracted with DCM (3×3 mL). The combined organic phases were dried (magnesium sulfate) and evaporated. Chromatography of the residue (3% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (70 mg). 1H NMR (400 MHz, CDCl3): 7.19 (d, J=8.6 Hz, 2H), 6.85 (d, J=8.6 Hz, 2H), 3.99 (t, J=6.4 Hz, 2H), 3.35 (s, 2H), 2.50-2.35 (m, 6H), 2.22 (s, 6H), 2.01-1.94 (m, 2H), 1.63-1.55 (m, 4H), 1.46-1.40 (m, 2H).

Provenance & Evidence