Butanal → 1-But-1-enylpyrrolidine

HRID 129100Notes

Reaction equation

HRID 129100 reaction equation
[CH:1](=O)[CH2:2][CH2:3][CH3:4].[NH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[N:6]1([CH:7]=[CH:8][CH2:9][CH3:10])[CH2:4][CH2:3][CH2:2][CH2:1]1

Participants

5

Reactant 3

HCID 261ButanalHCID 11430Potassium CarbonateHCID 31268Pyrrolidine

Product 1

HCID 1396491-But-1-enylpyrrolidineYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

108 g of freshly distilled butyraldehyde were added dropwise at 0° C. to a mixture of 213 g of pyrrolidine and 213 g of potassium carbonate. The mixture was allowed to stand overnight at room temperature, diluted with 300 ml of toluene, and the residue was filtered off. The filtrate was then subjected to vacuum distillation at 85° to 90° C. (80 mbar), giving 102 g of 97% pure 1-pyrrolidinobutene, which corresponds to 63.7% of the theoretical yield).

Workup

  1. filtrationthe residue was filtered off
  2. distillationThe filtrate was then subjected to vacuum distillation at 85° to 90° C. (80 mbar)

Sources & evidence

ORD record
ord-d3697e5b00e64347a24e9c7a729501b3
Source dataset
uspto-grants-1995_11
Patent number
US05466800

Reaction notes

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