Pyrrolidine → 1-[(3-Nitrophenyl)methyl]pyrrolidine

HRID 49811

Reaction equation

HRID 49811 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Br)([O-:3])=[O:2].[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

Product 1

HCID 7828801-[(3-Nitrophenyl)methyl]pyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-nitrobenzylbromide (3 g, 13.9 mmol) in anhydrous THF (30 ml) was added a solution of pyrrolidine (2.3 ml, 27.8 mmol) in anhydrous THF (10 ml) dropwise with stirring. Following the addition the mixture was stirred at ambient temperature overnight. The reaction mixture was filtered. The filter cake was washed with a small volume of anhydrous THF and the filtrate was concentrated to leave the intermediate 1-(3-nitrobenzyl)pyrrolidine as an oil. This oil was dissolved in methanol (50 ml) and three equivalents of both ammonium chloride and sodium sulfide nonahydrate were added. The mixture was heated to reflux for 2 hours. After cooling the mixture was filtered. The filtercake was washed with methanol and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and dried over sodium sulfate. Filtration and evaporation of solvent left 2i quantitatively as yellow crystals.

Workup

  1. additionthe addition the mixture
  2. stirringwas stirred at ambient temperature overnight
  3. filtrationThe reaction mixture was filtered
  4. washThe filter cake was washed with a small volume of anhydrous THF
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ae47483be0eb4f0581ed3c6a150e4a19
Source dataset
uspto-grants-2004_03
Patent number
US06710044B2

Linked notes

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