Triethylamine → 4-(4-Trifluoromethoxy-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 506861Notes

Reaction equation

HRID 506861 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].CCN(CC)CC.[F:21][C:22]([F:35])([F:34])[O:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:30]([C:27]2[CH:26]=[CH:25][C:24]([O:23][C:22]([F:21])([F:34])[F:35])=[CH:29][CH:28]=2)(=[O:32])=[O:31])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 523102p-(Trifluoromethoxy)benzenesulphonyl chloride

Product 1

HCID 458629304-(4-Trifluoromethoxy-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of piperazine-1-carboxylic acid tert-butyl ester (521 mg, 2.8 mmol) in DCM (6 ml) was added NEt3 (547 μl, 3.92 mmol, 1.4 eq.) and 4-trifluoromethoxy-benzenesulfonyl chloride (880 mg, 3.36 mmol, 1.2 eq.). The reaction mixture was stirred at room temperature for 12 hrs. The excess of sulfonyl chloride was quenched by addition of trisamine resin (150 mg), and subsequent stirring for 2 hrs. The resin was then filtered off, and NaHCO3 sat (5 ml) was added. Filtration of the resulting mixture through hydrophobic catridge and subsequent removal of the solvent under reduced pressure afforded the desired 4-(4-trifluoromethoxy-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester in quantitative yield.

Workup

  1. customThe excess of sulfonyl chloride was quenched by addition of trisamine resin (150 mg)
  2. stirringsubsequent stirring for 2 hrs
  3. filtrationThe resin was then filtered off
  4. additionwas added
  5. filtrationFiltration of the resulting mixture
  6. customthrough hydrophobic catridge and subsequent removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-1093c867f8d84d4886622b90325daad4
Source dataset
uspto-grants-2010_08
Patent number
US07786121B2

Reaction notes

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