Ammonium Chloride → HCID 68509550, compound

Participants

Reaction Steps

To a stirred suspension of 4-(4-allyloxycarbonyl-2-nitro-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (20.0 g, 49.33 mmol, 1.0 equiv) and Zn (23.22 g) 0.36 mol, 7.2 equiv) was added a sat. solution of NH4Cl (7.91 g, 0.15 mol, 3.0 equiv) and the reaction mixture heated to reflux. After 45 min, the reaction was cooled, filtered through Celite and concentrated by evaporation under reduced pressure. The filtrate was diluted with water and extracted with dichloromethane (3×200 mL). The combined organic fractions were washed with water, dried over Na2SO4 and concentrated by evaporation under reduced pressure. The brownish solid material was further washed with a mixture of hexane/ethyl acetate (98:2) to yield 15.7 g (85%) of the title product. 1H NMR (400 MHz, DMSO): δ 1.24-1.33 (m, 2H), 1.46 (s, 9H), 1.90-1.94 (m, 2H), 2.88-2.94 (m, 2H), 3.53-3.55 (m, 1H), 3.88-3.95 (m, 2H), 4.68 (d, J=5.2 Hz, 2H), 4.79 (s, 2H), 5.01 (d, J=7.5, 2H), 5.23 (d, J=10.4 Hz, 1H), 5.34 (d, J=17.3 Hz, 1H), 6.00-6.06 (m, 1H), 6.54 (d, J=8.2 Hz, 1H), 7.21 (m, 2H).

Provenance & Evidence