Potassium Carbonate → 1-(4-chlorophenethyl)-3-(R)-(+)-(1-cyano-1,1diphenylmethyl)piperidine

HRID 21385

反応式

HRID 21385 の反応式
[C:1]([C:3]([C@H:16]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)#[N:2].[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([CH2:27][CH2:28]Br)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([CH2:27][CH2:28][N:18]2[CH2:19][CH2:20][CH2:21][C@H:16]([C:3]([C:1]#[N:2])([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:17]2)=[CH:25][CH:24]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 230291-(2-Bromoethyl)-4-chlorobenzeneHCID 228537583-(R)-(1-cyano-1,1-diphenylmethyl)-piperidine

生成物 1

HCID 228537521-(4-chlorophenethyl)-3-(R)-(+)-(1-cyano-1,1diphenylmethyl)piperidine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture containing 3-(R)-(+)-(1-cyano-1,1-diphenylmethyl)piperidine (1 g--see Preparation 1), 4-chlorophenethyl bromide (0.72 g), anhydrous potassium carbonate (1.5 g) and acetonitrile (25 ml) was heated under reflux for 4 hours. The mixture was partitioned between dichloromethane (50 ml) and 10% aqueous potassium carbonate (30 ml), the layers separated, and the aqueous layer extracted with dichloromethane (3×30 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give an oil which was purified by column chromatography on silica eluting with hexane containing dichloromethane (30% up to 70%) and then dichloromethane containing methanol (0% up to 5%). The product-containing fractions were combined and concentrated in vacuo to give an oil which was crystallised from acetonitrile to give the title compound as colourless rhombs, yield 0.85 g, m.p. 129°14 131° C. [α]D25 +20.3 (c 1.0, CH2Cl2)

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. customThe mixture was partitioned between dichloromethane (50 ml) and 10% aqueous potassium carbonate (30 ml)
  4. customthe layers separated
  5. extractionthe aqueous layer extracted with dichloromethane (3×30 ml)
  6. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give an oil which
  9. customwas purified by column chromatography on silica eluting with hexane
  10. additioncontaining dichloromethane (30% up to 70%)
  11. additiondichloromethane containing methanol (0% up to 5%)
  12. concentrationconcentrated in vacuo
  13. customto give an oil which
  14. customwas crystallised from acetonitrile

出典と根拠

ORDレコード
ord-dd99be49ecbc46eba4904d687e239f52
出典データセット
uspto-grants-1995_06
特許番号
US05422358

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