Acetic Anhydride → N-ethyl-2-fluoroaniline

Participants

Reaction Steps

2-Fluoro-N-ethylaniline [NMR (DMSO-d6, 200 MHz): δ 1.16 (t, J=7.1 Hz, 3H); 3.11 (dq, J1 =7.2 Hz, J2 =6.5 Hz, 2H); 5.30 (br m, 1H); 6.48-6.59 (m, 1H); 6.70 (t, J=8.5 Hz, 1H); 6.92-7.06 (m, 2H)] was prepared from 2-fluoroaniline and acetic 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)-α-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N-ethyl-N-(2-fluorophenyl)benzamide as a light yellow wax. NMR (DMSO-d6, 200 MHz): δ 0.9 (d, J=6 Hz, 3H); 0.95 (d, J=6 Hz, 3H); 1.1 (t, J=7 Hz, 1H); 2.1 (m, 1H); 2.3 (m, 1H); 2.5 (m, 2H); 2.7 (m, 1H); 2.85 (m, 1H); 3.8 (br m, 2H); 4.8 (br s, 1H); 5.1 (d, J=10 Hz, 1H); 5.2 (d, J=17 Hz, 1H); 5.8 (m, 1H); 6.45 (m, 1H); 6.5 (s, 1H); 6.65 (m, 1H); 7.0-7.4 (m, 9H); 9.35 (s, 1H). [α]D20 =+3.4° (abs ethanol, c=2.04). Calc. for C31H36FN3O2HCl H2O: C, 66.95; H, 7.07; N, 7.56; Cl, 6.38. Found: C, 66.61; H, 7.14; N, 7.53; Cl, 6.40. Mass spectrum (CI--CH4) m/e: 502 (M+1, 89%), 501 (M, 17%), 348 (36%), 153 (100%).

Provenance & Evidence