Aniline → Benzenamine, N-propyl-

Participants

Reaction Steps

N-Propylaniline was prepared from aniline and propionic anhydride, coupled with 3-((αR)-α-((2S,5R)-4-allyl-2.5 -dimethyl-1-piperazinyl)-3-tert-butyldimethylsilyloxy)benzyl)benzoyl chloride, deprotected and purified by the methods described in Example 10 to give (+)-3-((αR)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N-phenyl-N-propylbenzamide as a light yellow solid. NMR (200 MHz, DMSO-d6): δ0.87 (t, J=7.4 Hz, 3H); 0.91 (d, J=5.9 Hz, 3H); 0.98 (d, J=6.0 Hz, 3H); 1.51 (m, 2H); 1.69 (dd, J1 =7.2 Hz, J2 =10.9 Hz, 1H); 2.06 (dd, J1 =7.0 Hz, J2 =10.5 Hz, 1H); 2.30 (d, J=10.3 Hz, 1H); 2.39-2.54 (m, 2H); 2.65 (br d, J=10.3 Hz, 1H); 2.85 (dd, J1 =7.4 Hz, J2 =14.5 Hz, 1H); 3.16 (dd, J1 =5.1 Hz, J2 =14.2 Hz, 1H); 3.79 (t, J=7,6 Hz, 2H); 4.77 (s, 1H); 5.12 (d, J=10.2 Hz, 1H); 5.18 (d, J=16.0 Hz, 1H); 5.71-5.84 (m, 1H); 6.43 (d, J=7.6 Hz, 1H); 6.57 (s,1H);6.64 (d, J=8.0 Hz, 1H); 7.02-7.33 (m, 10H); 9.32 (s, 1H).

Provenance & Evidence