Water → 2-(1-Benzylpyrrolidin-3-yl)ethanamine

HRID 867

Reaction equation

HRID 867 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][C:14]#[N:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][NH2:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 123645192-(1-Benzylpyrrolidin-3-yl)acetonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 446076812-(1-Benzylpyrrolidin-3-yl)ethanamineYield 99%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

14.7 g (0.0734 mole) (3RS)-1-benzyl-3-cyanomethyl pyrrolidine dissolved in 220 ml diethyl ether was slowly added to a slurry of 2.94 g of lithium aluminium hydride in 74 ml diethyl ether under an argon atmosphere. The mixture was stirred over night,and 6 ml water, 18 ml 3.75M NaOH-solution and 6 ml water was added to the mixture. The slurry was dried from excess of water with Na2SO4 /cellite, filtered by suction and evaporated to yield 14.84 g (99%) of the product.

Workup

  1. additionwas added to the mixture
  2. dry with materialThe slurry was dried from excess of water with Na2SO4 /cellite
  3. filtrationfiltered by suction
  4. customevaporated

Sources & evidence

ORD record
ord-355bf43961874334b0dd644d901cbbcf
Source dataset
uspto-grants-1998_03
Patent number
US05723444

Linked notes

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