Water → HCID 22038186, compound

HRID 1790417Notes

Reaction equation

HRID 1790417 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.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.O>C(Cl)(Cl)Cl>[CH3:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([S:27]([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:29])=[O:28])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 962WaterHCID 74014-Methoxybenzenesulfonyl chlorideHCID 22038045HCID 22038045, compound

Product 1

HCID 22038186HCID 22038186, compoundYield 23.6%

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-methoxybenzenesulfonyl chloride (95 mg) was added thereto and the resultant mixture was stirred at room temperature overnight. 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 (80 mg) was purified by NH-silica gel column chromatography (methanol/methylene chloride system) to give the title compound (45 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 (80 mg) was purified by NH-silica gel column chromatography (methanol/methylene chloride system)

Sources & evidence

ORD record
ord-2ba0c1ebc6474761a4ac0aa9a5bce8d5
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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