1,5-Dibromopentane → 3-Ethyl-4-(1-piperidinyl)benzonitrile

HRID 423302

反応式

HRID 423302 の反応式
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:10][CH3:11].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:10]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[N:1]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:6]#[N:7])[CH3:11]

参加物

5

反応物 3

HCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 27353304-Amino-3-ethylbenzonitrile

生成物 1

HCID 593167193-Ethyl-4-(1-piperidinyl)benzonitrile収率 18.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
160 °C

実験手順

4-Amino-3-ethylbenzonitrile (3.0 g, 20.5 mmol), 1,5-dibromopentane (11.1 mL, 82.1 mmol), potassium carbonate (5.67 g, 41.0 mmol) and water (39.6 mL) were all split equally between ten microwave vials and each heated at 160° C. for 1 h. All reaction mixtures were combined and extracted twice with ethyl acetate (40 mL) and the combined organic fractions dried (phase separator) and concentrated in vacuo. Dichloromethane was added and then the mixture filtered before the filtrate was purified by silica chromatography, eluting 2-5% ethyl acetate in hexane to give the title compound as a colourless oil (823 mg, 3.85 mmol). Analysis indicated that the compound contained a small dibromopentane impurity. δH (methanol-d4, 400 MHz) 7.52 (1H, dd), 7.47 (1H, dd), 7.13 (1H, d), 2.89 (4H, dd), 2.71 (2H, q), 1.76-1.71 (4H, m), 1.64-1.56 (2H, m), 1.25 (3H, t). MS (ES): C14H18N2 requires 214; found 215 (MH+).

後処理

  1. customall split equally between ten microwave vials
  2. customAll reaction mixtures
  3. extractionextracted twice with ethyl acetate (40 mL)
  4. customthe combined organic fractions dried (phase separator)
  5. concentrationconcentrated in vacuo
  6. additionDichloromethane was added
  7. filtrationthe mixture filtered before the filtrate
  8. customwas purified by silica chromatography
  9. washeluting 2-5% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-4c515ba76d7440ba856a52cfc26d76c0
出典データセット
uspto-grants-2012_01
特許番号
US08101775B2

関連ノート

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