(1,4-Dibenzylpiperazin-2-yl)-N,N-dimethylmethanamine → N,N-dimethyl-2-piperazinemethanamine

HRID 248456Notes

Reaction equation

HRID 248456 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:10][N:9](CC2C=CC=CC=2)[CH2:8][CH2:7][N:6]1CC1C=CC=CC=1)[CH3:3]>C(O)C.C1CCCCC1.C(O)(=O)C.[Pd]>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:10][NH:9][CH2:8][CH2:7][NH:6]1

Participants

6

Reactant 1

HCID 14664170(1,4-Dibenzylpiperazin-2-yl)-N,N-dimethylmethanamine

Product 1

HCID 14664185N,N-dimethyl-2-piperazinemethanamine

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 8078CyclohexaneSolvent

Procedure

A 4.7 g portion of 2-dimethylaminomethyl-1,4-bis(phenylmethyl)piperazine was dissolved in a mixture of 50 ml of ethanol, 20 ml of cyclohexane and 10 ml of glacial acetic acid. A 2.0 g portion of 10% palladium on carbon was added, the mixture was refluxed overnight and then filtered. The filtrate was evaporated, 5 ml of saturated aqueous potassium bicarbonate was added to the residue and this was extracted several times with dichloromethane. The extracts were combined, dried, filtered and evaporated, giving a gum which solidified on standing, giving 1.02 g of N,N-dimethyl-2-piperazinemethanamine.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. addition5 ml of saturated aqueous potassium bicarbonate was added to the residue
  5. extractionthis was extracted several times with dichloromethane
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customgiving a gum which

Sources & evidence

ORD record
ord-f962c2fba81642c2a6d4365241e98f34
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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