1-Phenethylamine → 1-(2-(1-Phenylethylamino)-4-fluorophenyl)-2,2,2-trifluoroethanone

HRID 1910542

반응식

HRID 1910542 반응식
[F:1][C:2]([F:14])([F:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1F)=[O:4].[C:15]1([CH:21]([NH2:23])[CH3:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[C:15]1([CH:21]([NH:23][C:6]2[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]=2[C:3](=[O:4])[C:2]([F:14])([F:13])[F:1])[CH3:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

5

반응물 3

HCID 74081-PhenethylamineHCID 81531DiisopropylethylamineHCID 247268371-(2,4-Difluorophenyl)-2,2,2-trifluoroethanone

생성물 1

HCID 587072761-(2-(1-Phenylethylamino)-4-fluorophenyl)-2,2,2-trifluoroethanone수율 12%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

2,2,2-Trifluoro-1-(2,4-difluorophenyl)ethanone (1.59 g, 7.57 mmol), 1-phenylethanamine (0.92 g, 7.57 mmol) and N,N-diisopropylethylamine (1.95 g, 15.1 mmol) were stirred at room temperature in dry acetonitrile (50 mL) for 20 h. The solvent was evaporated and the residue was dissolved in dichloromethane and washed with water. The dichloromethane was evaporated and purified by silica chromatography in 20% ethyl acetate in hexanes to collect the title compound (0.28 mg, 12% yield). 1H NMR (400 MHz, CDCl3): δ 9.32 (s, 1H), 7.80 (t, 1H), 7.31 (m, 5H), 6.33 (t, 1H), 6.22 (d, 1H), 4.58 (m, 1H), 1.62 (d, 3H).

후처리

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water
  4. customThe dichloromethane was evaporated
  5. custompurified by silica chromatography in 20% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-31c7d76f329b4d00a8f8112f0d3f3abc
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604021B2

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