Dimethyl Sulfoxide → 1-(3-Phenylpropionyl)-4-ketopiperidine

HRID 49445

반응식

HRID 49445 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]1([CH2:17][CH2:18][C:19]([N:21]2[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23][CH2:22]2)=[O:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl>[C:11]1([CH2:17][CH2:18][C:19]([N:21]2[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]2)=[O:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 221751621-(4-Hydroxypiperidin-1-yl)-3-phenylpropan-1-one

생성물 1

HCID 178176121-(3-Phenylpropionyl)-4-ketopiperidine수율 89.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매4회

실험 절차

To 1.68 mL of oxalyl chloride (19.2 mmol) in 35 mL of CH2Cl2 at −78° C. was added 2.73 mL (38.5 mmol) of dry DMSO in 5 mL of CH2Cl2. After the addition, 3.6 g (15.4 mmol) of 1-(3-phenylpropionyl)-4-hydroxypiperidine 134 in 5 mL of CH2Cl2 was added, and the mixture was stirred for 5 min in the cold. 10.73 mL (77 mmol) of triethylamine in 5 mL of CH2Cl2 was added, and the mixture was allowed to come to room temperature. The mixture was quenched with saturated aqueous ammonium chloride solution. The organic phase was washed with water twice, with saturated brine, dried, and evaporated under vacuum to give 3.2 g (89%) of 1-(3-phenylpropionyl)-4-ketopiperidine (135). GC/MS showed 100% purity with a molecular ion of 231.

후처리

  1. additionwas added
  2. customto come to room temperature
  3. customThe mixture was quenched with saturated aqueous ammonium chloride solution
  4. washThe organic phase was washed with water twice
  5. dry with materialwith saturated brine, dried
  6. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-c33b19de490b422a85936f15e5cda45d
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706740B2

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