Potassium Hydroxide → 1-(4-Methoxy-benzyl)-3-propyl-piperidine

HRID 228494ノート

反応式

HRID 228494 の反応式
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH2:11][CH:10]([C:14](=O)[CH2:15][CH3:16])[CH2:9]2)=[CH:5][CH:4]=1.[OH-].[K+].O.NN.[NH4+].[Cl-]>C(O)COCCO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][CH2:15][CH3:16])[CH2:9]2)=[CH:18][CH:19]=1

参加物

6

反応物 4

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 25517Ammonium ChlorideHCID 597303451-[1-(4-Methoxy-benzyl)-piperidin-3-yl]-propan-1-one

生成物 1

HCID 597300471-(4-Methoxy-benzyl)-3-propyl-piperidine収率 40%

試薬・触媒・溶媒 1

HCID 8117Diethylene Glycol溶媒

反応条件

温度
120 °C

実験手順

Combine 1-[1-(4-Methoxy-benzyl)-piperidin-3-yl]-propan-1-one (277.3 mg, 1.07 mmol), Diethylene glycol (10 mL), KOH (178.0 mg, 3.18 mmol), and Hydrazine-monohydrate (1.0 mL) at room temperature under a Nitrogen atmosphere. Heat the reaction mixture to 120° C. for 2 hours and then 220° C. for 4 hours. Cool reaction to room temperature and then pour the reaction mixture over sat NH4Cl (aq). Extract with Ethyl acetate, wash with brine, and dry over Na2SO4. Concentrate under reduced pressure and flash chromatograph using 3% 1N NH3 MeOH in CH2Cl2 to give 105.2 mg (40% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 0.9 (3H, t), 1.1-1.4 (4H, m), 1.5-1.7 (3H, m), 1.7 (1H, d), 1.9 (1H, td), 2.7-2.9 (2H, m), 3.5 (2H, dd), 3.8 (3H, s), 6.8 (2H, d), 7.2 (2H, d); MS m/z 248 (M+1).

後処理

  1. customat room temperature
  2. temperatureCool
  3. customreaction to room temperature
  4. additionpour the reaction mixture
  5. extractionExtract with Ethyl acetate
  6. washwash with brine
  7. dry with materialdry over Na2SO4
  8. concentrationConcentrate under reduced pressure and flash chromatograph

出典と根拠

ORDレコード
ord-e7a839a9a9434c49a918c0c32d82239f
出典データセット
uspto-grants-2009_07
特許番号
US07560463B2

反応ノート

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