2-Chlorobenzoxazole → HCID 15725118, compound

Participants

Reaction Steps

A mixture of 2-chloro-benzooxazole (8.00 g, 52.1 mmol, 1.0 equiv) and ethyl 4-amino-1-piperidine carboxylate (10.78 g, 62.5 mmol, 1.2 equiv) in anhydrous DMF (50 mL) was stirred at rt. A precipitate formed over night which was filtered off, the volume of the filtrate reduced and the residue taken up in ethyl acetate (10 mL). Precipitation of this solution from hexane provided an additional batch of the title compound as a white solid. Combined yield: 6.8 g (45%). 1H NMR (400 MHz, CDCl3): δ 1.27 (t, J=7.2 Hz, 3H), 1.48-1.52 (m, 2H), 2.14-2.18 (m, 2H), 3.09 (br t, 2H), 3.81-3.95 (m, 1H), 4.12-4.18 (m, 2H), 4.15 (q, J=7.2 Hz, 2H), 5.64 (br d, J=7.8 Hz, 1H), 7.04 (t, J=7.8 Hz, 1H), 7.17 (t, J=7.6 Hz, 1H), 7.25 (d, J=7.8 Hz, 1H), 7.36 (d, J=7.6 Hz, 1H). 13C NMR (100 MHz, CDCl3): δ 14.93, 32.53, 42.85, 50.66, 61.72, 109.00, 116.62, 121.24, 124.24, 143.10, 148.66, 155.72, 161.32. MS (ISP): 290.0 [M+H]+.

Provenance & Evidence