HCID 59605421, compound → 1-tert-Butyl-2-piperazinone

HRID 1922706Notes

Reaction equation

HRID 1922706 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:13](=[O:21])[CH2:12]1)=O)C1C=CC=CC=1>CCO.[Pd]>[C:17]([N:14]1[CH2:15][CH2:16][NH:11][CH2:12][C:13]1=[O:21])([CH3:20])([CH3:18])[CH3:19]

Participants

4

Reactant 1

HCID 59605421HCID 59605421, compound

Product 1

HCID 230810841-tert-Butyl-2-piperazinoneYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 10 mL round-bottomed flask was charged with a solution of 4-tert-butyl-3-oxopiperazine-1-carboxylic acid benzyl ester (0.75 g, 2.58 mmol) in EtOH (5 mL). The reaction mixture was flushed with nitrogen and 10% Pd/C (67 mg, 0.13 mmol) was added. The reaction mixture was stirred under a hydrogen atmosphere for 18 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the desired product was eluted using 2 M NH3 in MeOH to give 1-tert-Butylpiperazin-2-one as grey oil (0.276 g, 69%). 1H NMR (300 MHz, CDCl3): δ 3.50 (s, 2H), 3.37 (t, J=5.5 Hz, 2H), 3.06 (t, J=5.5 Hz, 2H), 1.48-1.41 (m, 9H)

Workup

  1. additionwas added
  2. washThe cartridge was washed with MeOH
  3. washthe desired product was eluted

Sources & evidence

ORD record
ord-86fb305c1b3c44b8936c4d07b4e2312c
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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