tert-Butyl piperazine-1-carboxylate → 1-Boc-4-(6-chloronaphthalen-2-ylsulfonyl)piperazine

HRID 278546Notes

Reaction equation

HRID 278546 reaction equation
C(=O)([O-])O.[Na+].[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].[Cl:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[CH:26]=[C:25]([S:30](Cl)(=[O:32])=[O:31])[CH:24]=[CH:23]2>C(OCC)(=O)C>[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([S:30]([C:25]2[CH:24]=[CH:23][C:22]3[C:27](=[CH:28][CH:29]=[C:20]([Cl:19])[CH:21]=3)[CH:26]=2)(=[O:31])=[O:32])[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 516892Sodium BicarbonateHCID 106351296-Chloronaphthalene-2-sulfonyl chloride

Product 1

HCID 187613901-Boc-4-(6-chloronaphthalen-2-ylsulfonyl)piperazineYield 91.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of aqueous sodium hydrogen carbonate (10 ml) solution, 1-tert-butoxycarbonylpiperazine (1.0 g) and ethyl acetate (10 ml), was added 6-chloronaphthalene-2-sulfonylchloride (1.4 g) and the mixture was stirred at room temperature for 1 hour and extracted with dichloromethane. The extract was washed with water, dried and concentrated. The residue was crystallized from diisopropylether to give colorless crystals of 1-(tert-butoxycarbonyl)-4-(6-chloro-naphthalene-2-sulfonyl)piperazine (2.02 g).

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was crystallized from diisopropylether

Sources & evidence

ORD record
ord-e8e5126dd3414b259b97b87086a30370
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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