Triethylamine → 4-[4-(2-Trifluoromethylbenzoyl)piperazin-1-yl]-benzonitrile

HRID 655605

반응식

HRID 655605 반응식
Cl.[N:2]1([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27](Cl)=[O:28]>ClCCl.O>[F:23][C:24]([F:34])([F:35])[C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27]([N:5]1[CH2:6][CH2:7][N:2]([C:8]2[CH:9]=[CH:10][C:11]([C:12]#[N:13])=[CH:14][CH:15]=2)[CH2:3][CH2:4]1)=[O:28]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 27339944-(Piperazin-1-yl)benzonitrile hydrochloride

생성물 1

HCID 114942194-[4-(2-Trifluoromethylbenzoyl)piperazin-1-yl]-benzonitrile수율 91%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a mixture of 4-piperazin-1-ylbenzonitrile hydrochloride (0.200 g, 0.890 mmol) in dichloromethane (15 mL) and triethylamine (0.452 g, 4.47 mmol) was added 2-trifluoromethylbenzoyl chloride (0.186 g, 0.890 mmol) at 0° C. The reaction mixture was warmed up to ambient temperature and stirred for 6 hours, then diluted with water, and extracted with dichloromethane. The organic phase was separated, washed with diluted HCl solution, sodium bicarbonate solution, brine, then dried over anhydrous MgSO4 and concentrated. The residue was purified by column chromatography and crystallization from n-hexane and the title compound was obtained as a white solid in 91% yield (0.294 g). 1H NMR (300 MHz, CDCl3) δ 7.72 (d, J=8.9 Hz, 1H), 7.54 (m, 4H), 7.36 (m, 1H), 6.84 (d, J=9.6 Hz, 2H), 3.94 (m, 2H), 3.33 (m, 6H). 13C NMR (75 MHz, CDCl3) δ 167.5, 153.0, 134.3, 133.6, 132.4, 129.5, 127.6, 127.2, 125.4, 121.8, 119.7, 114.9, 101.5, 47.3, 46.4, 41.2. MS (ES+) m/z 360.1 (M+1).

후처리

  1. extractionextracted with dichloromethane
  2. customThe organic phase was separated
  3. washwashed with diluted HCl solution, sodium bicarbonate solution, brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography and crystallization from n-hexane

출처 및 근거

ORD 기록
ord-b3070ebdfa9b41318fd3de4cbb17fe6f
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071603B2

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