Ethyl Acetate → tert-Butyl [4-(piperazin-1-yl)phenyl]carbamate

HRID 1267122Notes

Reaction equation

HRID 1267122 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][N:17](CC3C=CC=CC=3)[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].CCOC(C)=O>CCO.[Pd]>[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]2)=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 54469150Carbamic acid, [4-[4-(phenylmethyl)-1-piperazinyl]phenyl]-, 1,1-dimethylethyl ester

Product 1

HCID 16244582tert-Butyl [4-(piperazin-1-yl)phenyl]carbamateYield 53.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of [4-(4-benzyl-piperazine-1-yl)-phenyl)-carbamic acid tert-butyl ester (43.5 g) in EtOH (1 L) containing Pd/C 10% (4 g) was hydrogenated at room temperature. After 72 hours, the catalyst was removed by filtration and the filtrate was evaporated under reduced pressure. The oily residue was then purified by flash chromatography eluting with AcOEt/isopropylamine (90/10) and the solid obtained was recristallized from AcOEt to give the title compound (17.5 g) as white crystals.

Workup

  1. customwas hydrogenated at room temperature
  2. customthe catalyst was removed by filtration
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe oily residue was then purified by flash chromatography
  5. washeluting with AcOEt/isopropylamine (90/10)
  6. customthe solid obtained

Sources & evidence

ORD record
ord-e3e906b355324618b7b5f0b8b358330b
Source dataset
uspto-grants-2003_04
Patent number
US06552022B1

Reaction notes

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