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

HRID 1198582Notes

Reaction equation

HRID 1198582 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 108.68 g (2.860 mole) lithium aluminum hydride in 800 mL tetrahydrofuran, was added a solution of 194.5 g (0.790 mole) of N-ethyl-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamide in 600 mL tetrahydrofuran, dropwise under nitrogen. The reaction mixture was then refluxed four hours The reaction flask was cooled in an ice bath and treated dropwise successively with 108 mL of water, 108 mL of 15% sodium hydroxide, and 324 mL of water. 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 mixture was then refluxed four hours The reaction flask
  2. temperaturewas 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-06178848ca3548569486a1ecd52f257d
Source dataset
uspto-grants-1994_01
Patent number
US05281612

Reaction notes

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