Benzenesulfonyl chloride → HCID 69352330, compound

HRID 459832Notes

Reaction equation

HRID 459832 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[CH2:16][CH2:17][NH:18][CH2:19]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[CH2:16][CH2:17][N:18]([S:30]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:32])=[O:31])[CH2:19]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 210709471,1-Dimethylethyl 4-(1,2,3,4-tetrahydro-5-isoquinolinyl)-1-piperazinecarboxylate

Product 1

HCID 69352330HCID 69352330, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-(1,2,3,4-Tetrahydroisoquinolin-5-yl)-piperazine-1-carboxylic acid tert-butyl ester as a viscous oil (150 mg) from Step 3 was reacted with benzenesulfonyl chloride (60 microliters) using the Schotten-Baumann procedure (50 mL diethyl ether (Et2O) and 50 mL aqueous sodium carbonate). The ether layer was separated, dried over MgSO4, and concentrated in vacuo. The residue was chromatographed to provide 1.76 mg of 4-(2-benzenesulfonyl-1,2,3,4-tetrahydroisoquinolin-5-yl)-piperazine-1-carboxylic acid tert-butyl ester as a white solid.

Workup

  1. customThe ether layer was separated
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed

Sources & evidence

ORD record
ord-ccaec0c67ffe429a8212a12560212e66
Source dataset
uspto-grants-2007_03
Patent number
US07196088B2

Reaction notes

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