Pyridine → HCID 19807302, compound

HRID 1681176Notes

Reaction equation

HRID 1681176 reaction equation
N1C=CC=CC=1.Cl.[C:8]1(/[CH:14]=[CH:15]/[C:16]([NH:18][CH2:19][CH2:20][CH:21]2[CH2:26][CH2:25][N:24]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:23][CH2:22]2)=[O:17])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:34]([Cl:37])(=[O:36])[CH3:35]>O>[ClH:37].[C:8]1(/[CH:14]=[CH:15]/[C:16]([N:18]([C:34](=[O:36])[CH3:35])[CH2:19][CH2:20][CH:21]2[CH2:26][CH2:25][N:24]([CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:23][CH2:22]2)=[O:17])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 14553494HCID 14553494, compound

Product 1

HCID 19807302HCID 19807302, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A pyridine solution (5 ml) of (E)-3-phenyl-N-[2-(1-benzylpiperidin-4-yl)ethyl]-2-propenamide. hydrochloride (0.25 g) and acetyl chloride (0.3 ml) was stirred at 60° C. for 2 hours. Water was added to the reaction mixture after being left standing for cooling; the mixture was dried over anhydrous sodium sulfate. The solvent was distilled off. The oily residue was subjected to silica gel column chromatography (developing solvent : ethyl acetate). The solvent of the solution containing the object compound was distilled off. To the residue was added an ethanol solution of 3N hydrogen chloride. The solvent was then distilled off to obtain hydroscopic amorphous powder (0.16 g).

Workup

  1. waitafter being left
  2. temperaturefor cooling
  3. dry with materialthe mixture was dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. additionThe solvent of the solution containing the object compound
  6. distillationwas distilled off
  7. additionTo the residue was added an ethanol solution of 3N hydrogen chloride
  8. distillationThe solvent was then distilled off

Sources & evidence

ORD record
ord-553989b828b943e2a08f87e51f220b4c
Source dataset
uspto-grants-1992_12
Patent number
US05169856

Reaction notes

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