Water → (R)-N-Methyl-N-[1-(4-nitrophenyl)pyrrolidin-3-yl]acetamide

HRID 2426606Notes

Reaction equation

HRID 2426606 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][C@@H:12]([NH:15][C:16](=[O:18])[CH3:17])[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].I[CH3:22].O>CN(C=O)C>[CH3:22][N:15]([C@@H:12]1[CH2:13][CH2:14][N:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:11]1)[C:16](=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67147876(R)-N-[1-(4-Nitrophenyl)pyrrolidin-3-yl]acetamide

Product 1

HCID 67147828(R)-N-Methyl-N-[1-(4-nitrophenyl)pyrrolidin-3-yl]acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-N-[1-(4-Nitrophenyl)pyrrolidin-3-yl]acetamide (1.3 g) was added in portions to a suspension of sodium hydride (50% in oil; 0.25 g) in DMF (50 ml). After gas evolution had ceased, iodomethane (0.82 g) was added. After one hour, the reaction mixture was cautiously hydrolyzed with water and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated. This resulted in the product with the molecular weight of 263.30 (C13H17N3O3); MS (ESI): 264 (M+H+).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThis resulted in the product with the molecular weight of 263.30 (C13H17N3O3)

Sources & evidence

ORD record
ord-1f0575f9818d4b629a26ed0873d4aae9
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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