(1-Benzyl-pyrrolidin-3-ylmethyl)-ethyl-amine → Ethyl-pyrrolidin-3-ylmethyl-amine

HRID 464957Notes

Reaction equation

HRID 464957 reaction equation
[CH2:1]([NH:3][CH2:4][CH:5]1[CH2:9][CH2:8][N:7](CC2C=CC=CC=2)[CH2:6]1)[CH3:2].[H][H]>[Pd].C(O)C>[CH2:1]([NH:3][CH2:4][CH:5]1[CH2:9][CH2:8][NH:7][CH2:6]1)[CH3:2]

Participants

5

Reactant 2

HCID 5127972(1-Benzyl-pyrrolidin-3-ylmethyl)-ethyl-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 13491786Ethyl-pyrrolidin-3-ylmethyl-amineYield 74.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

A mixture of 151.65 g (0.695 mole) of N-ethyl-1-(phenylmethyl)-3-pyrrolidinemethanamine, 5 g of 20% palladium on carbon, and 1100 ml of ethanol was shaken in an atmosphere of hydrogen at about 50 psi and at room temperature for 21.6 hours. Another 5 g of 20% palladium on carbon was added and the hydrogenation continued for 24 hours. The catalyst was filtered and the filtrate evaporated under reduced pressure. The residue was distilled under vacuum, bp 88°-91° C. (11.5 mm), to give 66.0 g N-ethyl-3-pyrrolidinemethanamine.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe filtrate evaporated under reduced pressure
  3. distillationThe residue was distilled under vacuum, bp 88°-91° C. (11.5 mm)

Sources & evidence

ORD record
ord-7992297a356449abba865a25ee788e5e
Source dataset
uspto-grants-1985_10
Patent number
US04550103

Reaction notes

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