N-((1-Benzylpyrrolidin-3-yl)methyl)cyclopropanamine → N-(Pyrrolidin-3-ylmethyl)cyclopropanamine

HRID 2372055Notes

Reaction equation

HRID 2372055 reaction equation
C1(C[N:8]2[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][CH:15]3[CH2:17][CH2:16]3)[CH2:9]2)C=CC=CC=1.[H][H]>[Pd].CO>[CH:15]1([NH:14][CH2:13][CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)[CH2:17][CH2:16]1

Participants

5

Reactant 2

HCID 14280886N-((1-Benzylpyrrolidin-3-yl)methyl)cyclopropanamineHCID 178418361HCID 178418361, compound

Product 1

HCID 13491801N-(Pyrrolidin-3-ylmethyl)cyclopropanamineYield 76.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 13.6 g (59.0 mmol) of 1-(phenylmethyl)-N-cyclopropyl-3-pyrrolidinemethanamine, 0.5 g of 20% palladium on carbon and 140 ml of methanol was shaken in an atmosphere of hydrogen at about 4.5×105Pa and room temperature for 24 hours. The catalyst was removed by filtering through Celite, the filtrate concentrated and distilled in vacuo to give 6.3 g of N-cyclopropyl-3-pyrrolidinemethanamine, bp 88-90°/13 mm.

Workup

  1. customThe catalyst was removed
  2. filtrationby filtering through Celite
  3. concentrationthe filtrate concentrated
  4. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-0e18884f57b04154a278f01abab55c94
Source dataset
uspto-grants-1992_03
Patent number
US05097032

Reaction notes

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