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

HRID 464966Notes

Reaction equation

HRID 464966 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 50 psi 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° C. (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-6fcd801cf5694ce19ae4126e31ca4947
Source dataset
uspto-grants-1985_10
Patent number
US04550103

Reaction notes

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