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

HRID 620847Notes

Reaction equation

HRID 620847 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([NH:9][C:10]([CH:12]1[CH2:16][C:15](=O)[N:14]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13]1)=O)[CH3:8].O.[OH-].[Na+]>O1CCCC1>[CH2:7]([NH:9][CH2:10][CH:12]1[CH2:16][CH2:15][N:14]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:13]1)[CH3:8]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 13491793N-ethyl-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 5127972(1-Benzyl-pyrrolidin-3-ylmethyl)-ethyl-amineYield 88.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 108.8 g (2.86 mole) lithium aluminum hydride in 800 ml tetrahydrofuran, was added a solution of 194.5 g (0.79 mole) of N-ethyl-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamide in 600 ml tetrahydrofuran dropwise under nitrogen. The reaction was then refluxed four hours. The reaction flask was cooled in an ice bath and 108 ml of water, 108 ml of 15% sodium hydroxide, and 324 ml of water were added. The precipitated solids were filtered and washed with hot ethanol. The combined filtrates were concentrated, then dissolved in dichloromethane, filtered, dried over magnesium sulfate, and the solvent evaporated under reduced pressure to give 151.9 g of N-ethyl-1-(phenylmethyl)-3-pyrrolidinemethanamine as an oil.

Workup

  1. temperatureThe reaction was then refluxed four hours
  2. temperatureThe reaction flask was cooled in an ice bath
  3. filtrationThe precipitated solids were filtered
  4. washwashed with hot ethanol
  5. concentrationThe combined filtrates were concentrated
  6. dissolutiondissolved in dichloromethane
  7. filtrationfiltered
  8. dry with materialdried over magnesium sulfate
  9. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-52099216f2e847c886f928af0e07cfdc
Source dataset
uspto-grants-1989_04
Patent number
US04822801

Reaction notes

Loading…