Water → 1-(phenylmethyl)-N-propyl-3-pyrrolidinemethanamine

HRID 980709Notes

Reaction equation

HRID 980709 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][CH2:23][CH2:24][CH3:25])=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][CH2:23][CH2:24][CH3:25])[CH2:11]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 134917985-oxo-1-(phenylmethyl)-N-propyl-3-pyrrolidinecarboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 142808851-(phenylmethyl)-N-propyl-3-pyrrolidinemethanamine

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, 12.0 g (45.6 mmole) of solid 5-oxo-1-(phenylmethyl)-N-propyl-3-pyrrolidinecarboxamide. When the addition was complete, the reaction mixture was stirred at room temperature for 18 hours and then at reflux 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 9.6 g of 1-(phenylmethyl)-N-propyl-3-pyrrolidine methanamine, as a heavy syrup.

Workup

  1. additionwas added portionwise
  2. additionWhen the addition
  3. temperatureat reflux 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-7dab02147bea4be2851644e4e1c1e2a4
Source dataset
uspto-grants-1987_01
Patent number
US04638067

Reaction notes

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