Acryloyl chloride → HCID 18504850, compound

HRID 457772Notes

Reaction equation

HRID 457772 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][C:19]([C:23]([NH2:25])=[O:24])=[CH:18][CH:17]=3)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[C:28](Cl)(=[O:31])[CH:29]=[CH2:30]>CC(C)=O>[C:28]([N:15]1[C:16]2[C:21](=[CH:20][C:19]([C:23]([NH2:25])=[O:24])=[CH:18][CH:17]=2)[CH:22]=[C:14]1[N:11]1[CH2:10][CH2:9][CH:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:13][CH2:12]1)(=[O:31])[CH:29]=[CH2:30]

Participants

5

Reactant 3

HCID 13140Acryloyl chlorideHCID 14797Potassium HydroxideHCID 54483006HCID 54483006, compound

Product 1

HCID 18504850HCID 18504850, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.318 g (1 mmol) of (4-benzylpiperidinyl)-indole-5-carboxamide was taken in 15 mL dry acetone and was reacted with 0.2 g (5 mmol) of powdered KOH for 15 Min. The mixture was cooled in ice and 0.225 mg (2.5 mmol) of acryloyl chloride was added in one lot. Stirring continued at 0° C. for 20 Min., after which the reaction was further stirred at room temp. for 1 h. the solvent was removed in vacuo and the residue was extracted with ethyl acetate from water. The extract was dried and evaporated. TLC (ethyl acetate-hexane) and mass spectrum (M+ at 372) confirmed the desired product. This product was used without further purification for the next step.

Workup

  1. temperatureThe mixture was cooled in ice
  2. customcontinued at 0° C. for 20 Min
  3. stirring, after which the reaction was further stirred at room temp. for 1 h. the solvent
  4. customwas removed in vacuo
  5. extractionthe residue was extracted with ethyl acetate from water
  6. customThe extract was dried
  7. customevaporated
  8. customThis product was used without further purification for the next step

Sources & evidence

ORD record
ord-26b39e49ce524e319f15d00bfd2a1f41
Source dataset
uspto-grants-2007_03
Patent number
US07189739B2

Reaction notes

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