HCID 18669100, compound → tert-Butyl 4-(3-hydroxyphenyl)piperazine-1-carboxylate

HRID 1058954Notes

Reaction equation

HRID 1058954 reaction equation
C1(C[O:8][C:9]2[CH:10]=[C:11]([N:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)[CH:12]=[CH:13][CH:14]=2)C=CC=CC=1>CO.C(OCC)(=O)C.CO.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:10]=[C:11]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 1

HCID 18669100HCID 18669100, compound

Product 1

HCID 18669061tert-Butyl 4-(3-hydroxyphenyl)piperazine-1-carboxylateYield 93.1%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

A slurry of palladium hydroxide on carbon (330 mg) in methanol (10 mL) was added to a solution of 1,1-dimethylethyl 4-[3-(phenylmethoxy)phenyl]-1-piperazinecarboxylate (Description 20, 3.25 g, 8.8 mmol) in ethyl acetate/methanol (1:9) and the mixture was shaken under an atmosphere of hydrogen (40 psi) for 48 h. The mixture was filtered through celite and the solvent was evaporated under reduced pressure to give the title compound (2.28 g, 93%). 1H NMR (360 MHz, CDCl3) δ1.48 (9H, s), 3.10-3.13 (4H, m), 3.54-3.57 (4H, m), 6.34 (1H, dd, J 7.9, 2.2 Hz), 6.41 (1H, t, J 2.0 Hz), 6.34 (1H, dd, J 8.3, 2.2 Hz), and 7.11 (1H, t, J 7.9 Hz).

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-05e9d76ef4e64451a230a8a1cc83e05a
Source dataset
uspto-grants-2003_02
Patent number
US06518273B1

Reaction notes

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