Water → HCID 22038173, compound

HRID 1790405Notes

Reaction equation

HRID 1790405 reaction equation
N1CCN([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][CH2:8]2)CC1.Br[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1.C([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])C.O.[CH3:36]N(C)C=O>>[N+:25]([C:22]1[CH:23]=[CH:24][C:19]([CH2:18][CH2:17][N:30]2[CH2:31][CH2:32][CH:36]([N:7]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH2:9][CH2:8]3)[CH2:34][CH2:33]2)=[CH:20][CH:21]=1)([O-:27])=[O:26]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 8471TriethylamineHCID 792664-Nitrophenethyl bromideHCID 22038430HCID 22038430, compound

Product 1

HCID 22038173HCID 22038173, compound

Procedure

1-(Piperazin-4-yl)indoline (2.00 g) was dissolved in dimethylformamide (20 ml) and 4-(2-bromoethyl)nitrobenzene (10.0 g) and triethylamine (2.9 ml) were added thereto followed by stirring the resultant mixture at 100° C. overnight. After adding water to the reaction solution, extracted with ethyl acetate, the organic layer was washed with brine and dried over magnesium sulfate. After distilling off the solvent, the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (1.05 g) as a slightly yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. distillationAfter distilling off the solvent
  5. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-3368bc5eb73f47f98ef2b13d0303d0e8
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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