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

HRID 423302

반응식

HRID 423302 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 593167193-Ethyl-4-(1-piperidinyl)benzonitrile수율 18.8%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
160 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-4c515ba76d7440ba856a52cfc26d76c0
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101775B2

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