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

HRID 1198586Notes

Reaction equation

HRID 1198586 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-prop-yl-3-pyrrolidinemethanamine, 1.0 g of 20% palladium on carbon and 140 mL of methanol was shaken in an atmosphere of hydrogen at about 4.5×105Pa at 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-76e7f8e1f0084aab81f5779b2b774643
Source dataset
uspto-grants-1994_01
Patent number
US05281612

Reaction notes

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