Water → HCID 70283941, compound

HRID 976143Notes

Reaction equation

HRID 976143 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.C(=O)([O-])[O-].[K+].[K+].[NH:16]1[CH2:21][CH2:20][CH:19](/[CH:22]=[CH:23]/[C:24]([C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=2)=[O:25])[CH2:18][CH2:17]1.O>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][N:16]1[CH2:21][CH2:20][CH:19](/[CH:22]=[CH:23]/[C:24]([C:26]2[CH:27]=[CH:28][C:29]([N+:32]([O-:34])=[O:33])=[CH:30][CH:31]=2)=[O:25])[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 680073-Fluorobenzyl bromideHCID 70282403HCID 70282403, compound

Product 1

HCID 70283941HCID 70283941, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.11 g of 3-fluorobenzylbromide and 2.53 g of potassium carbonate were added to 3.0 g of (E)-4-[3-(piperidin-4-yl)propenoyl]nitrobenzene dissolved in 30 ml of dimethylformamide at room temperature, and the mixture was stirred for 2 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The obtained residue was applied to silica gel column chromatography to obtain 1.06 g of the title compound as pale yellow crystal.

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5d696bac736b405d94e57e480015b379
Source dataset
uspto-grants-1997_03
Patent number
US05610303

Reaction notes

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