2-Nitrobenzoyl chloride → HCID 16962631, compound

HRID 644220Notes

Reaction equation

HRID 644220 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:14]([C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](Cl)=[O:20])([O-:16])=[O:15]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:19](=[O:20])[C:18]2[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=2[N+:14]([O-:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 118752-Nitrobenzoyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 16962631HCID 16962631, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-(tert-butoxycarbonyl)piperazine (11.18 g, 60 mmol) in CH2Cl2 (120 mL) at 0° C. was added 2-nitrobenzoyl chloride (8.0 mL, 60.6 mmol). The reaction was warmed to room temperature and stirred for 2 hours. A solution of 50% satd Na2 CO3 was added and the mixture was extracted with CH2Cl2. The organic layer was washed with satd citric acid and water, dried over MgSO4, and concentrated to a slurry. Ether was added to the mixture and it was filtered to give the desired product as a white solid (16.0 g, 79%).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with CH2Cl2
  3. washThe organic layer was washed with satd citric acid and water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to a slurry
  6. additionEther was added to the mixture and it
  7. filtrationwas filtered

Sources & evidence

ORD record
ord-35c271ff1b82420e9181976f841cdd93
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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