Potassium Carbonate → Tert-butyl 4-(4-hydroxybenzoyl)piperazine-1-carboxylate

HRID 856108Notes

Reaction equation

HRID 856108 reaction equation
C([O:4][C:5]1[CH:25]=[CH:24][C:8]([C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[O:10])=[CH:7][CH:6]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([N:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:15][CH2:16]2)=[O:10])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 23081258Tert-butyl 4-(4-acetoxybenzoyl)piperazine-1-carboxylate

Product 1

HCID 23081232Tert-butyl 4-(4-hydroxybenzoyl)piperazine-1-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 4-(4-acetoxybenzoyl)piperazine-1-carboxylate (18.5 g, 53.1 mmol) prepared in Reference Example 195 and potassium carbonate (370 mg, 2.65 mmol) in methanol (200 ml) was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, 5% hydrochloric acid and methylene chloride were added to the residue, and the mixture was vigorously stirred. The resulting precipitates were collected by filtration, and washed with water and methylene chloride, and then dried in vacuo to afford tert-butyl 4-(4-hydroxybenzoyl)piperazine-1-carboxylate (14.9 g, yield 92%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, 5% hydrochloric acid and methylene chloride
  2. additionwere added to the residue
  3. stirringthe mixture was vigorously stirred
  4. customThe resulting precipitates
  5. filtrationwere collected by filtration
  6. washwashed with water and methylene chloride
  7. customdried in vacuo

Sources & evidence

ORD record
ord-e52381af043e4e9a893a40def6f93b7c
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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