Benzenepropanoyl chloride → N-(1-[9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl]-4-piperidyl)-3-phenylpropionamide

Participants

Reaction Steps

Using a procedure similar to that described in Example 27 except starting with 4-amino-1-[9,10-dihydro-9,10-methanoanthracen-9-ylmethyl]piperidine (described in Example 8b) and 3-phenylpropionyl chloride, the title compound was obtained as a white solid (46%) by crystallization from ether-ethyl acetate, mp 149.0°-50.0° C.; MS(CI): 437 (M+H); NMR (300 Hz, DMSO-d6): 1.20-1.40(m, 2H), 1.55-1.69(m, 2H), 2.17-2.40(m, 4H), 2.44(s, 2H), 2.79(t, 2H, J=8.1 Hz), 2.85-2.98(m, 2H), 3.33(m, 2H), 3.53(m, 1H), 4.30(s, 1H), 6.85-6.98(m, 4H), 7.10-7.32(m, 9H), 7.66(d, 1H, J=7.5 Hz).

Provenance & Evidence