Water → HCID 22037888, compound

HRID 1790416Notes

Reaction equation

HRID 1790416 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)[CH2:6][CH2:5]1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.O>C(Cl)(Cl)Cl>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH:1][CH2:2][CH2:3][N:4]2[CH2:9][CH2:8][CH:7]([N:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:12][CH2:11]3)[CH2:6][CH2:5]2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73984-Chlorobenzenesulfonyl chlorideHCID 22038045HCID 22038045, compound

Product 1

HCID 22037888HCID 22037888, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-[1-(2-Aminoethyl)piperidin-4-yl]indoline (113 mg) was dissolved in chloroform (3 ml). Under ice cooling, 4-chlorobenzenesulfonyl chloride (97 mg) was added thereto and the resultant mixture was stirred for 6 hr. After adding water, the reaction solution was extracted with chloroform. The organic layer was washed with brine and dried over magnesium sulfate. After evaporating the solvent, the resulting residue (205 mg) was purified by NH-silica gel column chromatography (methanol/methylene chloride system) to give the title compound (134 mg) as an oil.

Workup

  1. extractionthe reaction solution was extracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporating the solvent
  5. customthe resulting residue (205 mg) was purified by NH-silica gel column chromatography (methanol/methylene chloride system)

Sources & evidence

ORD record
ord-0f91c50ccd684cd2b7b7bf9f1aa760b3
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

Loading…