1-Benzyl-3-benzylmethylaminomethyl-3-methoxypyrrolidine → [(3-Methoxypyrrolidin-3-YL)methyl](methyl)amine

HRID 2400085Notes

Reaction equation

HRID 2400085 reaction equation
C([N:8]1[CH2:12][CH2:11][C:10]([CH2:15][NH:16][CH2:17]CC2C=CC=CC=2)([O:13][CH3:14])[CH2:9]1)C1C=CC=CC=1>CO.Cl.[Pd]>[CH3:14][O:13][C:10]1([CH2:15][NH:16][CH3:17])[CH2:11][CH2:12][NH:8][CH2:9]1

Participants

5

Reactant 1

HCID 193821871-Benzyl-3-benzylmethylaminomethyl-3-methoxypyrrolidine

Product 1

HCID 15282082[(3-Methoxypyrrolidin-3-YL)methyl](methyl)amine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

8.4 g (20 mmol) of 80% strength 1-benzyl-3-benzylmethylaminomethyl-3-methoxypyrrolidine are dissolved in 100 of methanol, 4.4 ml of concentrated hydrochloric acid are added and the mixture is hydrogenated on 4 g of 10% strength Pd/active carbon at 80° C. and 120 bar. The catalyst is filtered off, the solution is concentrated, a solution of 3 g of KOH in 50 ml of methanol are added, KCl is filtered off and the solution is concentrated. The residue is taken up in CHCl3 again, the mixture is filtered, the solution is concentrated and the residue is distilled.

Workup

  1. additionare added
  2. filtrationThe catalyst is filtered off
  3. concentrationthe solution is concentrated
  4. additiona solution of 3 g of KOH in 50 ml of methanol are added
  5. filtrationKCl is filtered off
  6. concentrationthe solution is concentrated
  7. filtrationthe mixture is filtered
  8. concentrationthe solution is concentrated
  9. distillationthe residue is distilled

Sources & evidence

ORD record
ord-9478616cdf844e83a4df69bddc939876
Source dataset
uspto-grants-1995_09
Patent number
US05453422

Reaction notes

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