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

HRID 2426605Notes

Reaction equation

HRID 2426605 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][N:12]([CH:16]1[CH2:20][CH2:19][NH:18][CH2:17]1)[C:13](=[O:15])[CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH3:11][N:12]([CH:16]1[CH2:20][CH2:19][N:18]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:17]1)[C:13](=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 10796Cesium carbonateHCID 130411303-(N-Acetyl-N-methylamino)pyrrolidine

Product 1

HCID 21105631N-methyl-N-[1-(4-nitrophenyl)pyrrolidin-3-yl]acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Fluoronitrobenzene (25.0 g) was slowly added to a suspension of N-methyl-N-pyrrolidin-3-ylacetamide (25.2 g) and cesium carbonate (57.6 g) in DMF (300 ml). After 2 hours, the reaction mixture was poured into water, and the resultant precipitate was filtered off with suction. Alternatively, the product can also be extracted with ethyl acetate and purified by chromatography after concentration. This results in the product with the molecular weight of 263.30 (C13H17N3O3): MS (ESI): 264 (M+H+).

Workup

  1. filtrationthe resultant precipitate was filtered off with suction
  2. extractionAlternatively, the product can also be extracted with ethyl acetate
  3. custompurified by chromatography
  4. concentrationafter concentration
  5. customThis results in the product with the molecular weight of 263.30 (C13H17N3O3)

Sources & evidence

ORD record
ord-e431602dcf7f42f685b218c40a12d73d
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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