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

HRID 974962ノート

反応式

HRID 974962 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c10e94ed41c246c99adeef3f417d9968
出典データセット
uspto-grants-1997_03
特許番号
US05607950

反応ノート

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