Water → 1-tert-Butoxycarbonyl-4-[(5-chloro-1-phenylsulfonylindol-2-yl)sulfonyl]piperazine

HRID 352770Notes

Reaction equation

HRID 352770 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12])[C:6]([S:20](Cl)(=[O:22])=[O:21])=[CH:5]2.[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25].C(N(CC)CC)C.O>ClCCl>[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][N:34]([S:20]([C:6]2[N:7]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:8]3[C:4]([CH:5]=2)=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=3)(=[O:22])=[O:21])[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:25])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 235137375-Chloro-1-phenylsulfonylindole-2-sulfonyl chloride

Product 1

HCID 227103001-tert-Butoxycarbonyl-4-[(5-chloro-1-phenylsulfonylindol-2-yl)sulfonyl]piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-chloro-1-phenylsulfonylindole-2-sulfonyl chloride (4.41 g) in dichloromethane (75 ml), tert-butyl-1-piperazine carboxylate (2.21 g) and triethylamine (1.65 ml) were added under ice cooling. The resulting mixture was stirred at room temperature for 3 hours. After completion of the reaction, water and dichloromethane were added to the reaction mixture. The organic layer so separated was dried over anhydrous sodium sulfate and then distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (ethyl acetate:n-hexane=1:20), whereby the title compound (3.63 g, 60%) was obtained as colorless crystals.

Workup

  1. additionwere added to the reaction mixture
  2. customThe organic layer so separated
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by chromatography on a silica gel column (ethyl acetate:n-hexane=1:20), whereby the title compound (3.63 g, 60%)
  7. customwas obtained as colorless crystals

Sources & evidence

ORD record
ord-a659112ac9b6468db18a5dd985b245dd
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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