Water → tert-Butyl (2R)-4-cyclobutyl-2-(piperazin-1-ylcarbonyl)piperazine-1-carboxylate

HRID 603193Notes

Reaction equation

HRID 603193 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C@H:16]2[CH2:21][N:20]([CH:22]3[CH2:25][CH2:24][CH2:23]3)[CH2:19][CH2:18][N:17]2[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:15])[CH2:10][CH2:9]1)C1C=CC=CC=1.O>[Pd].C(O)C>[CH:22]1([N:20]2[CH2:19][CH2:18][N:17]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@@H:16]([C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[O:15])[CH2:21]2)[CH2:23][CH2:24][CH2:25]1

Participants

5

Reactant 2

HCID 962WaterHCID 57656643tert-butyl (2R)-2-[(4-benzylpiperazin-1-yl)carbonyl]-4-cyclobutylpiperazine-1-carboxylate

Product 1

HCID 57656912tert-Butyl (2R)-4-cyclobutyl-2-(piperazin-1-ylcarbonyl)piperazine-1-carboxylateYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on carbon (900 mg) was added to tert-butyl (2R)-2-[(4-benzylpiperazin-1-yl)carbonyl]-4-cyclobutylpiperazine-1-carboxylate (5.12 g) and water (10 ml). Under an argon atmosphere, ethanol (250 μl) was added and the mixture stirred at room temperature under a hydrogen filled balloon. After 4 hours the catalyst was removed by filtration and washed with a small quantity of non-flammable solvent (dichloromethane). The combined filtrate was concentrated in vacuo, azeotroped once with toluene and dried under vacuum to give tert-butyl (2R)-4-cyclobutyl-2-(piperazin-1-ylcarbonyl)piperazine-1-carboxylate as an off-white foam (4.08 g).

Workup

  1. customAfter 4 hours the catalyst was removed by filtration
  2. washwashed with a small quantity of non-flammable solvent (dichloromethane)
  3. concentrationThe combined filtrate was concentrated in vacuo
  4. customazeotroped once with toluene
  5. customdried under vacuum

Sources & evidence

ORD record
ord-57aa8c34144e4bceae1983977d0a33c8
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

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