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

HRID 349138Notes

Reaction equation

HRID 349138 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[C:11]([NH:14][CH:15]1[CH2:19][CH2:18][NH:17][CH2:16]1)(=[O:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].O>CN1C(=O)CCC1>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:17]2[CH2:18][CH2:19][CH:15]([NH:14][C:11](=[O:13])[CH3:12])[CH2:16]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 5227153-Acetamidopyrrolidine

Product 1

HCID 12067826N-[1-(4-nitrophenyl)pyrrolidin-3-yl]acetamideYield 100.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

After dissolving 56.4 g of 1-fluoro-4-nitrobenzene (0.4 mol) and 51.2 g of 3-acetamido-pyrrolidine (0.4 mol) in 400 ml of NMP, 66.4 g of potassium carbonate (0.48 mol) are added under a nitrogen atmosphere and the mixture is heated at 100° C. for 18 hours. The reaction medium is allowed to cool and is then poured into 2 l of water. The yellow precipitate formed is filtered off, washed with water and then dried in a vacuum oven over P2O5. 100 g (100%) of N-[1-(4-nitrophenyl)pyrrolidin-3-yl]acetamide (1) are thus obtained in the form of a yellow solid.

Workup

  1. additionare added under a nitrogen atmosphere
  2. temperatureto cool
  3. customThe yellow precipitate formed
  4. filtrationis filtered off
  5. washwashed with water
  6. dry with materialdried in a vacuum oven over P2O5

Sources & evidence

ORD record
ord-ea925050ecd34d62988dc15c47dfe8f7
Source dataset
uspto-grants-2007_02
Patent number
US07179301B2

Reaction notes

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