1-(phenylmethyl)-N-propyl-3-pyrrolidinemethanamine → N-propyl-3-pyrrolidinemethanamine

HRID 464963Notes

Reaction equation

HRID 464963 reaction equation
C1(C[N:8]2[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][CH2:15][CH2:16][CH3:17])[CH2:9]2)C=CC=CC=1.[H][H]>[Pd].CO>[CH2:15]([NH:14][CH2:13][CH:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)[CH2:16][CH3:17]

Participants

5

Reactant 2

HCID 142808851-(phenylmethyl)-N-propyl-3-pyrrolidinemethanamineHCID 178418361HCID 178418361, compound

Product 1

HCID 13491799N-propyl-3-pyrrolidinemethanamineYield 83.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 14.0 g (60.0 mmole) of 1-(phenylmethyl)-N-propyl-3-pyrrolidinemethanamine, 1.0 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 7.1 g of N-propyl-3-pyrrolidinemethanamine, bp 49°-50° C. (0.25 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-7924d2d2baa34b25ac154a596efd1a2b
Source dataset
uspto-grants-1985_10
Patent number
US04550103

Reaction notes

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