Acetic Anhydride → N-ethyl-2-fluoroaniline

HRID 1900275Notes

Reaction equation

HRID 1900275 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:9](O[C:13](=O)[CH3:14])(=O)[CH3:10].[CH2:16]([N:19]1[C@H:24]([CH3:25])[CH2:23][N:22]([C@H:26]([C:41]2[CH:42]=[C:43]([CH:47]=[CH:48][CH:49]=2)[C:44](Cl)=[O:45])[C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([O:33][Si](C(C)(C)C)(C)C)[CH:28]=2)[C@@H:21]([CH3:50])[CH2:20]1)[CH:17]=[CH2:18]>>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][CH2:9][CH3:10].[CH2:16]([N:19]1[C@H:24]([CH3:25])[CH2:23][N:22]([C@H:26]([C:41]2[CH:42]=[C:43]([CH:47]=[CH:48][CH:49]=2)[C:44]([N:4]([CH2:13][CH3:14])[C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[F:1])=[O:45])[C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=2)[C@@H:21]([CH3:50])[CH2:20]1)[CH:17]=[CH2:18]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 95842-FluoroanilineHCID 111350383-((alphaR)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-(tert-butyldimethylsilyloxy)benzyl)benzoyl chloride

Product 2

HCID 2737180N-ethyl-2-fluoroanilineHCID 54105729HCID 54105729, compound

Procedure

2-Fluoro-N-ethylaniline [NMR (DMSO-d6, 200 MHz): δ1.16 (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): δ0.9 (d, J=6 Hz, 3H); 0.95 (d, J=6 Hz, 3H); 1.1 (t, J=7 Hz, 3H); 1.7 (m, 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%).

Workup

  1. custompurified by the methods

Sources & evidence

ORD record
ord-d22fee74b9cf4de39070b612c1562423
Source dataset
uspto-grants-1996_11
Patent number
US05574159

Reaction notes

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