Water → 1-(3-Methylbut-1-en-1-yl)pyrrolidine

HRID 416678Notes

Reaction equation

HRID 416678 reaction equation
[CH:1](=O)[CH2:2][CH:3]([CH3:5])[CH3:4].[NH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.O>C1(C)C=CC=CC=1>[N:7]1([CH:1]=[CH:2][CH:3]([CH3:5])[CH3:4])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 962WaterHCID 115523-MethylbutanalHCID 31268Pyrrolidine

Product 1

HCID 586199651-(3-Methylbut-1-en-1-yl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

194 g (2.25 mol) of isovaleraldehyde are diluted in 1115 ml of toluene and cooled to 0° C. with stirring. 190.3 g (2.68 mol) of pyrrolidine, dissolved in 185.8 ml of toluene, were then added dropwise to this solution, such that the reaction temperature did not rise above 5° C. After the addition had ended, the reaction solution was stirred at 5° C. for another 1 hour. Subsequently, the mixture was warmed to room temperature and the water formed was removed completely by extraction with toluene. Thereafter, the solvent was removed by evaporation and the crude product (329.1 g; 95% of theory) was stored at 4° C. in a refrigerator.

Workup

  1. additionwere then added dropwise to this solution, such that the reaction temperature
  2. customdid not rise above 5° C
  3. additionAfter the addition
  4. stirringthe reaction solution was stirred at 5° C. for another 1 hour
  5. temperatureSubsequently, the mixture was warmed to room temperature
  6. customwas removed completely by extraction with toluene
  7. customThereafter, the solvent was removed by evaporation
  8. customwas stored at 4° C. in a refrigerator

Sources & evidence

ORD record
ord-b4a0a949210a456491d9434c683265d8
Source dataset
uspto-grants-2012_01
Patent number
US08088954B2

Reaction notes

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