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

HRID 978567Notes

Reaction equation

HRID 978567 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 4.5×105Pa 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-3b38af692ad64bfc90ae4a89ef259ac5
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

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