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

HRID 1354660
Notes
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Reaction equation

HRID 1354660 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6228
Dimethylformamide
Solvent

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-fcadeb1a2868451aa48fa7d875d05b01
Source dataset
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07223788B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes