tert-butyl 5-(5-chloro-2-ethoxyphenyl)-2H-1,4-oxazine-4(3H)-carboxylate → 3-(5-Chloro-2-ethoxyphenyl)morpholine

Participants

Reaction Steps

This compound was prepared from tert-butyl 5-(5-chloro-2-ethoxyphenyl)-2H-1,4-oxazine-4(3H)-carboxylate using procedures similar to those described in Example 3b above. Platinum oxide was used as a catalyst. The product was isolated as a brown solid (38% yield); 1H-NMR (d6-DMSO) 1.34 (3H, s), 2.87-3.00 (3H, m), 3.42 (2H, m), 3.72-3.76 (2H, m), 4.02-4.11 (3H, m), 6.97 (1H, d), 7.25 (1H, d), 7.47 (1H, brs); 13C-NMR (d6-DMSO) 14.6, 45.9, 52.9, 63.7, 66.5, 71.1, 113.2, 126.9, 127.5; MS ES(+) 242.8 (M++1); HRMS m/z calcd for C12H16ClNO2+H+ 242.0948 [M+H+]. Found 242.0958. IR λmax=1491, 1103, 806 cm−1.

Provenance & Evidence