Ethyl 4-amino-1-piperidinecarboxylate → HCID 68695765, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-methylsulfanyl-benzooxazole-5-sulfonic acid dimethylamide (1.43 g, 5.25 mmol, 1.0 equiv) and ethyl 4-amino-1-piperidine carboxylate (1.36 g, 7.88 mmol, 1.5 equiv) in anhydrous DMAc (7.5 mL) was heated to 100° C. for 48 h. The solution was concentrated by evaporation under reduced pressure and the crude reaction product purified with column chromatography on silica eluting with ethyl acetate/hexane (2:1) to give 1.40 g (67%) of the title compound. 1H NMR (300 MHz, DMSO): δ 1.19 (t, J=7.1 Hz, 3H), 1.37-1.49 (m, 2H), 1.94-1.99 (m, 2H), 2.59 (s, 6H), 2.94-3.02 (m, 2H), 3.80-3.83 (m, 1H), 3.91-3.95 (m, 2H), 4.04 (q, J=7.1 Hz, 2H), 7.39 (dd, J=8.2 Hz, J=1.8 Hz, 1H), 7.53 (d, J=1.8 Hz, 1H), 7.59 (d, J=8.2 Hz, 1H), 8.39 (d, J=7.6 Hz, 1H). 13C NMR (75 MHz, DMSO): δ 14.56, 31.07, 37.62, 42.05, 49.70, 60.65, 108.88, 114.22, 120.40, 130.37, 143.98, 150.67, 154.59, 162.76. MS (ISP): 397.0 [M+H]+.

Provenance & Evidence