4-(((2R)-1,4-dibenzyl-2-piperazinyl)methyl)-3,3-dimethyl-2-piperazinone → 3,3-dimethyl-4-((2R)-2-piperazinylmethyl)-2-piperazinone

HRID 1972595Notes

Reaction equation

HRID 1972595 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11](CC2C=CC=CC=2)[CH2:10][C@@H:9]1[CH2:21][N:22]1[CH2:27][CH2:26][NH:25][C:24](=[O:28])[C:23]1([CH3:30])[CH3:29])C1C=CC=CC=1>CO>[CH3:29][C:23]1([CH3:30])[N:22]([CH2:21][C@H:9]2[CH2:10][NH:11][CH2:12][CH2:13][NH:8]2)[CH2:27][CH2:26][NH:25][C:24]1=[O:28]

Participants

3

Reactant 1

HCID 665835354-(((2R)-1,4-dibenzyl-2-piperazinyl)methyl)-3,3-dimethyl-2-piperazinone

Product 1

HCID 665823733,3-dimethyl-4-((2R)-2-piperazinylmethyl)-2-piperazinoneYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(((2R)-1,4-dibenzyl-2-piperazinyl)methyl)-3,3-dimethyl-2-piperazinone (0.500 g, 1.23 mmol) was dissolved in MeOH (25 mL). This solution was passed through an H-Cube™ flow hydrogenator (ThalesNano Technology, Budapest, Hungary) via the solvent inlet using a 10% Pd/C CatCart™ (30 mm cartridge length, source ThalesNano, pre-washed and hydrogenated at full H2 mode for 10 min at 1 mL/min) at 1 mL/min flow rate in full H2 mode at 60° C. The solution collected was concentrated in vacuo to give 3,3-dimethyl-4-((2R)-2-piperazinylmethyl)-2-piperazinone (0.27 g) as a colorless solid.

Workup

  1. washa 10% Pd/C CatCart™ (30 mm cartridge length, source ThalesNano, pre-washed and hydrogenated at full H2 mode for 10 min at 1 mL/min) at 1 mL/min flow rate in full H2 mode at 60° C
  2. customThe solution collected
  3. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-07336192db59474b8e7a780d9753f981
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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