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

HRID 1786546Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1786546
[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

Komponenten

5

Edukt 4

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

Produkt 1

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

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b9d361fa95a640f9a04b086442faf109
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07507760B2

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