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Sodium Chloride → 4-(tert-Butoxycarbonyl)-2,2-dimethyl-1-[4-(pyridin-4-yl)benzoyl]piperazine

HRID 352830
Notes
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Reaction equation

HRID 352830 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][C:10]([CH3:15])([CH3:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:30]=[CH:29][C:25]([C:26]([O-])=[O:27])=[CH:24][CH:23]=2)=[CH:18][CH:17]=1.[Cl-].[Na+]>CN(C)C=O.C(N(CC)CC)C.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:26](=[O:27])[C:25]2[CH:24]=[CH:23][C:22]([C:19]3[CH:18]=[CH:17][N:16]=[CH:21][CH:20]=3)=[CH:30][CH:29]=2)[C:10]([CH3:15])([CH3:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 5234Sodium ChlorideHCID 227103871-Boc-3,3-dimethylpiperazineHCID 227111444-(4-Pyridyl)benzoate

Product 1

HCID 227107644-(tert-Butoxycarbonyl)-2,2-dimethyl-1-[4-(pyridin-4-yl)benzoyl]piperazine

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent
HCID 6344
Dichloromethane
Solvent
HCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-(tert-butoxycarbonyl)-3,3-dimethylpiperazine (173 mg) in a mixture of N,N-dimethylformamide (2.5 ml) and triethylamine (1.0 ml) was added (4-nirophenyl) 4-(4-pyridyl)benzoate (330 mg). The resulting mixture was stirred at 60° C. for 5 days. The reaction mixture was diluted with methylene chloride and then added with a saturated aqueous solution of sodium chloride to form two layers. The organic layer obtained by separation was washed with a saturated aqueous solution of sodium bicarbonate and an aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crudely purified product was purified by chromatography on a silica gel column (methylene chloride:methanol=50:1), whereby the title compound (199 mg) was obtained as colorless amorphous.

Workup

  1. customto form two layers
  2. customThe organic layer obtained by separation
  3. washwas washed with a saturated aqueous solution of sodium bicarbonate
  4. dry with materialan aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crudely purified product was purified by chromatography on a silica gel column (methylene chloride:methanol=50:1), whereby the title compound (199 mg)
  7. customwas obtained as colorless amorphous

Sources & evidence

ORD record
ord-275e5b49534645a393c00e5c79668fb3
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06747023B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes