Triethylamine → 4-[4-Hydroxy-4-(2-hydroxy-ethyl)-piperidin-1-yl]-2-trifluoromethyl-benzonitrile

HRID 1919305ノート

反応式

HRID 1919305 の反応式
[OH:1][CH2:2][CH2:3][C:4]1([OH:10])[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.C(N(CC)CC)C.F[C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:20]=1>CN(C)C=O.O>[OH:10][C:4]1([CH2:3][CH2:2][OH:1])[CH2:9][CH2:8][N:7]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([C:27]([F:28])([F:30])[F:29])[CH:20]=2)[CH2:6][CH2:5]1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 6050854-Fluoro-2-(trifluoromethyl)benzonitrileHCID 219359914-(2-Hydroxyethyl)piperidin-4-ol

生成物 1

HCID 675011244-[4-Hydroxy-4-(2-hydroxy-ethyl)-piperidin-1-yl]-2-trifluoromethyl-benzonitrile収率 68%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of compound 26 (517 mg, 3.25 mmol) in anhydrous dimethylformamide (15 mL) under argon were added triethylamine (1.32 g, 13.0 mmol) and 4-fluoro-2-trifluoromethylbenzonitrile (1.80 g, 9.52 mmol). The solution was stirred at 80° C. for 4 hrs. The solution was cooled at room temperature and poured in water (100 mL), extracted with diethyl ether (3×25 mL), washed with brine and finally dried over magnesium sulphate. Purification of the resulting crude product by flash chromatography using ethyl acetate/hexane (7:3) as an eluant gave the desired compound 27a (687 mg, 68%). 1H NMR (400 MHz, Acetone-d6) δ: 1.74 (m, 6H), 3.45 (m, 2H), 3.85 (m, 4H), 7.24 (dd, 1H, J1=6.4 Hz, J2=2.5 Hz), 7.32 (d, 1H, J=2.4 Hz), 7.72 (d, 1H, J=8.8 Hz).

後処理

  1. temperatureThe solution was cooled at room temperature
  2. extractionextracted with diethyl ether (3×25 mL)
  3. washwashed with brine
  4. dry with materialfinally dried over magnesium sulphate
  5. customPurification of the resulting crude product by flash chromatography

出典と根拠

ORDレコード
ord-0a019d58ec734354b8e2b222769af3a9
出典データセット
uspto-grants-2012_05
特許番号
US08168627B2

反応ノート

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