Acetonitrile → (R)-2-[(1-Benzyl-pyrrolidin-3-yl)methyl-amino]-N,N-diphenyl-acetamide

HRID 1786546

반응식

HRID 1786546 반응식
[C:1]([N:9]1[CH2:13][CH2:12][C@@H:11](NC)[CH2:10]1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:17][C:18]([N:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19].C([O-])(O)=O.[Na+].C[C:39]#[N:40]>>[CH2:1]([N:9]1[CH2:13][CH2:12][C@H:11]([CH2:39][NH:40][CH2:17][C:18]([N:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:19])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 4

HCID 6342AcetonitrileHCID 2320412-Bromo-n,n-diphenylacetamideHCID 516892Sodium BicarbonateHCID 70216545(R)-(1-benzoyl-pyrrolidin-3-yl)-methyl-amine

생성물 1

HCID 69053726(R)-2-[(1-Benzyl-pyrrolidin-3-yl)methyl-amino]-N,N-diphenyl-acetamide

실험 절차

To a solution of (R)-(1-benzoyl-pyrrolidin-3-yl)-methyl-amine(0.32 g, 1.68 mmol) in dry CH3CN (10 ml) was added 2-bromo-N,N-diphenyl acetamide(0.49 g, 1.68 mmol) and NaHCO3 (0.28 g, 3.36 mmol) under nitrogen. The reaction mixture was refluxed overnight. After cooling, the solvent was evaporated. The residue was taken up with water (5 ml) and extracted with CHCl3 (3×25 ml). The organic was dried over MgSO4 and evaporated to dryness. The resulting residue was purified by column chromatography using CH2Cl2:CH3OH (15:1) to give 680 mg of desired product.

후처리

  1. temperatureThe reaction mixture was refluxed overnight
  2. temperatureAfter cooling
  3. customthe solvent was evaporated
  4. extractionextracted with CHCl3 (3×25 ml)
  5. dry with materialThe organic was dried over MgSO4
  6. customevaporated to dryness
  7. customThe resulting residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-b9d361fa95a640f9a04b086442faf109
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07507760B2

연결된 노트

불러오는 중…