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

HRID 980705Notes

Reaction equation

HRID 980705 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, is 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 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-c750651f19bd40a59e16a9c31ac2ff68
Source dataset
uspto-grants-1987_01
Patent number
US04638067

Reaction notes

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