Water → (1-Benzyl-pyrrolidin-3-ylmethyl)-isopropyl-amine

HRID 868112Notes

Reaction equation

HRID 868112 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O=[C:8]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][CH:10]([C:20]([NH:22][CH:23]([CH3:25])[CH3:24])=O)[CH2:9]1.O.[OH-].[Na+]>O1CCCC1>[C:14]1([CH2:13][N:12]2[CH2:8][CH2:9][CH:10]([CH2:20][NH:22][CH:23]([CH3:25])[CH3:24])[CH2:11]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 47935185-oxo-1-(phenylmethyl)-N-(2-propyl)3-pyrrolidinecarboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 14280887(1-Benzyl-pyrrolidin-3-ylmethyl)-isopropyl-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 8.2 g (0.2 mole) of lithium aluminum hydride in 150 ml of dry tetrahydrofuran was added portionwise, 18.3 g (70.0 mmole) of solid 5-oxo-1-(phenylmethyl)-N-(2-propyl)-3-pyrrolidinecarboxamide. When the addition was compete, the reaction mixture was stirred at room temperature for 18 hours and then refluxed for two hours. After cooling to room temperature, the mixture was treated dropwise, successively, with 8 ml of water, 8 ml of 15% aqueous sodium hydroxide and 24 ml of water, titrating the final addition to produce a granular precipitate. The solid was removed by filtration, washed with tetrahydrofuran and the filtrate evaporated in vacuo to give 15.6 g of 1-(phenylmethyl)-N-(2-propyl)-3-pyrrolidinemethanamine as a heavy syrup.

Workup

  1. additionwas added portionwise
  2. additionWhen the addition
  3. temperaturerefluxed for two hours
  4. temperatureAfter cooling to room temperature
  5. additionthe mixture was treated dropwise
  6. additionaddition
  7. customto produce a granular precipitate
  8. customThe solid was removed by filtration
  9. washwashed with tetrahydrofuran
  10. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-1fea0c78af124760a9b348be3a27ca5f
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

Loading…