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

HRID 1988985Notes

Reaction equation

HRID 1988985 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11](CC2C=CC=CC=2)[CH2:10][CH:9]1[CH2:21][N:22]([CH3:24])[CH3:23])C1C=CC=CC=1>CCO.[Pd]>[CH3:23][N:22]([CH3:24])[CH2:21][CH:9]1[CH2:10][NH:11][CH2:12][CH2:13][NH:8]1

Participants

4

Reactant 1

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

Product 1

HCID 14664185N,N-dimethyl-2-piperazinemethanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

{[1,4-bisbenzylpiperazin-2-yl]methyl}dimethylamine (1 equivalent), was dissolved in EtOH and the solution was transferred to a stainless steel high pressure vessel equipped with a pressure gauge. 10% Pd/C was added (10 wt. %), and the vessel charged with H2. The reaction mixture was stirred at 130° C. and 200 psi of H2 overnight. The reaction mixture was cooled to room temperature, filtered over a pad of Celite, and then evaporated. The desired amine was obtained in quantitative yield as a pale yellow oil. GC/MS: 143 (10%, M+), Rt=14.3 minutes.

Workup

  1. customthe solution was transferred to a stainless steel high pressure vessel
  2. customequipped with a pressure gauge
  3. additionthe vessel charged with H2
  4. custom200 psi of H2 overnight
  5. temperatureThe reaction mixture was cooled to room temperature
  6. filtrationfiltered over a pad of Celite
  7. customevaporated

Sources & evidence

ORD record
ord-b8cff0ae258a431bac6dce3aee5c0250
Source dataset
uspto-grants-2010_01
Patent number
US07642278B2

Reaction notes

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