Dimethylformamide → 1-Benzyl-2-piperidone

HRID 259752노트

반응식

HRID 259752 반응식
[H-].[Na+].[C:3]1(=[O:9])[NH:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CN(C)C=O>C1(C)C=CC=CC=1>[CH2:10]([N:8]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 126652-PiperidoneHCID 24758Sodium hydride

생성물 1

HCID 51700761-Benzyl-2-piperidone수율 42.3%

시약·촉매·용매 1

HCID 1140Toluene용매3회

실험 절차

To a suspension of sodium hydride (80%, 3.3 g, 0.11 mol) in dry toluene (250 ml) under argon, was added dropwise a solution of δ-valerolactam (9.9 g, 0.10 mol) in toluene (50 ml). When the addition was complete, the mixture was heated under reflux for 1 h, then cooled to ambient temperature. A solution of benzyl bromide (13 ml, 18.8 g, 0.11 mol) in toluene (50 ml) containing dimethyl formamide (1 ml) was then added dropwise over 15 minutes. The resulting mixture was heated under reflux for 4 h. On cooling, the mixture was filtered and the filtrate was dried (Na2SO4) and evaporated in vacuo to give an oil. Bulb-to-bulb distillation gave the title compound (D26) as a yellow oil (8.0 g).

후처리

  1. additionWhen the addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 h
  4. additionwas then added dropwise over 15 minutes
  5. temperatureThe resulting mixture was heated
  6. temperatureunder reflux for 4 h
  7. temperatureOn cooling
  8. filtrationthe mixture was filtered
  9. dry with materialthe filtrate was dried (Na2SO4)
  10. customevaporated in vacuo
  11. customto give an oil
  12. distillationBulb-to-bulb distillation

출처 및 근거

ORD 기록
ord-46712f5af6e442ae81975eac26efe3ca
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05523299

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