Water → Tert-butyl 4-(4-iodobenzoyl)piperazine-1-carboxylate

HRID 1804112Notes

Reaction equation

HRID 1804112 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].[OH-].[Na+].O>O1CCCC1.C(OCC)(=O)C>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([I:1])=[CH:3][CH:4]=2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 743734-Iodobenzoyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 44157877Tert-butyl 4-(4-iodobenzoyl)piperazine-1-carboxylateYield 93.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Iodobenzoyl chloride (7.99 g) and piperazine-1-carboxylic acid tert-butyl ester (5.87 g) were dissolved in tetrahydrofuran (75 ml), 1N aqueous sodium hydroxide solution (36 mL) was added, and the mixture was stirred at room temperature. The reaction mixture was poured into water under cooling and 1N aqueous sodium hydroxide solution and ethyl acetate were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N aqueous sodium hydroxide solution and saturated brine, then washed with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. To the residue was added hexane and the mixture was stirred at room temperature. The crystals were collected by filtration to give the title compound (11.67 g).

Workup

  1. temperatureunder cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with 1N aqueous sodium hydroxide solution and saturated brine
  4. washwashed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. additionTo the residue was added hexane
  8. stirringthe mixture was stirred at room temperature
  9. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-fcf6b3232deb4b138d42e85992254604
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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