Phenethyl bromide → 3-(R,S)-(1-carbamoyl-1,1-diphenylmethyl)-1-phenethylpiperidine

HRID 21397

反応式

HRID 21397 の反応式
[C:1]([C:4]([CH:17]1[CH2:22][CH2:21][CH2:20][NH:19][CH2:18]1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:3])[NH2:2].[CH2:23](Br)[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:4]([CH:17]1[CH2:22][CH2:21][CH2:20][N:19]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:18]1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:3])[NH2:2]

参加物

5

反応物 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 136337483-(R,S)-(1-carbamoyl-1,1-diphenylmethyl)piperidine

生成物 1

HCID 212240933-(R,S)-(1-carbamoyl-1,1-diphenylmethyl)-1-phenethylpiperidine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture containing 3-(R,S)-(1-carbamoyl-1,1-diphenylmethyl)piperidine (0.3 g), phenethyl bromide (0.2 g), anhydrous potassium carbonate (0.3 g) and acetonitrile (10 ml) was heated under reflux for 7 hours. The mixture was partitioned between dichloromethane (30 ml) and 10% aqueous sodium carbonate (30 ml), the layers separated, and the aqueous layer extracted with dichloromethane (2×30 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give a colourless solid which was recrystallised from aqueous ethanol to give the title compound, yield, 0.17 g, m.p. 175°-1780° C.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 7 hours
  3. customThe mixture was partitioned between dichloromethane (30 ml) and 10% aqueous sodium carbonate (30 ml)
  4. customthe layers separated
  5. extractionthe aqueous layer extracted with dichloromethane (2×30 ml)
  6. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give a colourless solid which
  9. customwas recrystallised from aqueous ethanol

出典と根拠

ORDレコード
ord-978206fb8dd144ab90f2e261895a7ce5
出典データセット
uspto-grants-1995_06
特許番号
US05422358

関連ノート

読み込み中…