tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-[(6-bromo-2-naphthyl)sulfonyl]piperazinecarboxylate

HRID 278551Notes

Reaction equation

HRID 278551 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].C(=O)([O-])O.[Na+].[Br: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:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:30]([C:25]2[CH:24]=[CH:23][C:22]3[C:27](=[CH:28][CH:29]=[C:20]([Br:19])[CH:21]=3)[CH:26]=2)(=[O:31])=[O:32])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 516892Sodium BicarbonateHCID 144577416-Bromonaphthalene-2-sulfonyl chloride

Product 1

HCID 22628201Tert-butyl 4-[(6-bromo-2-naphthyl)sulfonyl]piperazinecarboxylateYield 92.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-tert-butoxycarbonylpiperazine (1.25 g), sodium hydrogen carbonate solution (10 ml) and ethyl acetate (10 ml), was added 6-bromonaphthalene-2-sulfonylchloride (2.05 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 with diisopropylether to give 1-(tert-butoxycarbonyl)-4-(6-bromonaphthalene-2-sulfonyl)piperazine as colorless crystals (2.83 g).

Workup

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

Sources & evidence

ORD record
ord-d9c7864150174d4f9d402bdf7acd0002
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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