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

HRID 655605

反応式

HRID 655605 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b3070ebdfa9b41318fd3de4cbb17fe6f
出典データセット
uspto-grants-2011_12
特許番号
US08071603B2

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