Water → HCID 67748299, compound

HRID 1079410Notes

Reaction equation

HRID 1079410 reaction equation
[C:1]([N:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:30](Cl)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.O>C(O)C>[C:1]([N:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH:18]1[CH2:23][CH2:22][N:21]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:20][CH2:19]1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 67748307HCID 67748307, compound

Product 1

HCID 67748299HCID 67748299, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(N-acetyl-N-hexylaminophenyloxy)piperidine (1.4 g) in ethanol (10 ml) were added potassium carbonate (1.2 g) and benzyl chloride (0.54 g) and the mixture was heated under reflux overnight. Water was added to the reaction mixture, which was extracted with ethyl acetate (50 ml×3). The combined extract was dried over anhydrous sodium sulfate and the solvent was distilled off. The residue was purified by silica gel column chromatography (developing solvent: methylene chloride/methanol =10/1 (v/v)) to obtain 4-(N-acetyl-N-hexylaminophenyloxy)-1-phenylmethylpiperidine (1.2 g) as a pale yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. extractionwas extracted with ethyl acetate (50 ml×3)
  4. extractionThe combined extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by silica gel column chromatography (developing solvent: methylene chloride/methanol =10/1 (v/v))

Sources & evidence

ORD record
ord-e6a0807dbf5b43f995e9c7c142335c4c
Source dataset
uspto-grants-1996_12
Patent number
US05580883

Reaction notes

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