(1-Benzyl-pyrrolidin-3-ylmethyl)-isopropyl-amine → N-(Pyrrolidin-3-ylmethyl)propan-2-amine

HRID 464969Notes

Reaction equation

HRID 464969 reaction equation
C1(C[N:8]2[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][CH:15]([CH3:17])[CH3:16])[CH2:9]2)C=CC=CC=1.[H][H]>[Pd].CO>[CH3:16][CH:15]([NH:14][CH2:13][CH:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)[CH3:17]

Participants

5

Reactant 2

HCID 14280887(1-Benzyl-pyrrolidin-3-ylmethyl)-isopropyl-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 13491802N-(Pyrrolidin-3-ylmethyl)propan-2-amineYield 76.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 13.4 g (58.0 mmol) of 1-phenylmethyl-N-(2-propyl)-3-pyrrolidinemethanamine, 1.0 g of 20% palladium on carbon and 130 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 filtration through Celite; the filtrate concentrated and distilled in vacuo to give 6.3 g of N-(2-propyl)-3-pyrrolidinemethanamine, bp 58°-60° C. (3.5 mm).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate concentrated
  3. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-ef852e02f3304acd9306175be4fecffa
Source dataset
uspto-grants-1985_10
Patent number
US04550103

Reaction notes

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