Potassium Hydroxide → 3-Butyl-1-(4-methoxy-benzyl)-piperidine

HRID 228500

반응식

HRID 228500 반응식
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH2:11][CH:10]([C:14](=O)[CH2:15][CH2:16][CH3:17])[CH2:9]2)=[CH:5][CH:4]=1.[OH-].[K+].O.NN.[NH4+].[Cl-]>C(O)COCCO>[CH2:14]([CH:10]1[CH2:11][CH2:12][CH2:13][N:8]([CH2:7][C:6]2[CH:19]=[CH:20][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:9]1)[CH2:15][CH2:16][CH3:17]

참가 물질

6

반응물 4

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 25517Ammonium ChlorideHCID 597301981-[1-(4-Methoxy-benzyl)-piperidin-3-yl]-butan-1-one

생성물 1

HCID 597304013-Butyl-1-(4-methoxy-benzyl)-piperidine수율 89%

시약·촉매·용매 1

HCID 8117Diethylene Glycol용매

반응 조건

온도
120 °C

실험 절차

Combine 1-[1-(4-Methoxy-benzyl)-piperidin-3-yl]-butan-1-one (356.0 mg, 0.95 mmol), Diethylene glycol (15 mL), KOH (479.0 mg, 8.54 mmol), and Hydrazine-monohydrate (1.8 mL) at room temperature under a Nitrogen atmosphere. Heat the reaction mixture to 120° C. for 2 hours and then 220° C. for 24 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 220.7 mg (89% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 0.7-0.9 (3H, m), 1.1-1.4 (4H, m), 1.5-1.7 (4H, m), 1.7 (1H, d), 1.9 (1H, t), 2.8 (2H, t), 3.4 (2H, dd), 3.6-3.7 (3H, m), 3.8 (3H, s), 6.8 (2H, d), 7.2 (2H, d); MS m/z 262 (M+1).

후처리

  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

출처 및 근거

ORD 기록
ord-777cd9e8c37d4ae192acd6077e7596a1
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560463B2

연결된 노트

불러오는 중…