Phenethyl bromide → 4-(2-Carbamoyl-2,2-diphenylethyl)-1-phenethylpiperidine

HRID 974962Notes

Reaction equation

HRID 974962 reaction equation
[C:1]([C:4]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)(=[O:3])[NH2:2].[CH2:24](Br)[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:4]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:8][CH2:7]1)(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 199701994-(2-Carbamoyl-2,2-diphenylethyl)piperidine

Product 1

HCID 98445774-(2-Carbamoyl-2,2-diphenylethyl)-1-phenethylpiperidineYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(2-carbamoyl-2,2-diphenylethyl)piperidine (300 mg, 0.97 mmol) (Preparation 3), phenethyl bromide (198 mg, 1.07 mmol) and potassium carbonate (400 mg) in acetonitrile (10 ml) was heated under reflux for 6 hours, allowed to cool to room temperature and evaporated. The residue was partitioned between dichloromethane and 10% aqueous potassium carbonate solution and the aqueous layer was extracted twice into dichloromethane. The combined organic layers were dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica using dichloromethane plus 0-10% methanol as eluant. Appropriate fractions were combined and evaporated to give the title compound (195 mg, 49%) as a colourless foam, which was characterised as a hydrate.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. customevaporated
  4. customThe residue was partitioned between dichloromethane and 10% aqueous potassium carbonate solution
  5. extractionthe aqueous layer was extracted twice into dichloromethane
  6. dry with materialThe combined organic layers were dried over magnesium sulphate
  7. customevaporated
  8. customThe residue was purified by chromatography on silica
  9. customevaporated

Sources & evidence

ORD record
ord-c10e94ed41c246c99adeef3f417d9968
Source dataset
uspto-grants-1997_03
Patent number
US05607950

Reaction notes

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