Potassium Iodide → HCID 21311313、化合物

HRID 1584166

反応式

HRID 1584166 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].[OH:22][C:23]1[CH:31]=[CH:30][C:26]([CH2:27][CH2:28]Cl)=[CH:25][C:24]=1[O:32][CH3:33].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[C:1]([C:3]([C@H:16]1[CH2:21][CH2:20][CH2:19][N:18]([CH2:28][CH2:27][C:26]2[CH:30]=[CH:31][C:23]([OH:22])=[C:24]([O:32][CH3:33])[CH:25]=2)[CH2:17]1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)#[N:2]

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 212240924-Hydroxy-3-methoxyphenethyl chlorideHCID 228537583-(R)-(1-cyano-1,1-diphenylmethyl)-piperidine

生成物 1

HCID 21311313HCID 21311313、化合物

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 (0.3 g), 4-hydroxy-3-methoxyphenethyl chloride (0.233 g--see Preparation 6), anhydrous potassium carbonate (0.5 g), potassium iodide (0.2 g) and acetonitrile (15 ml) was heated under reflux for 5 hours. The mixture was partitioned between dichloromethane (40 ml) and 10% aqueous potassium 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 foam which was purified by column chromatography on silica eluting with dichloromethane containing methanol (5%). The product-containing fractions were combined and concentrated in vacuo to give a gum which was crystallised from acetonitrile to give the title compound as colourless rhombs, yield 0.132 g, m.p. 159-160°.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. customThe mixture was partitioned between dichloromethane (40 ml) and 10% aqueous potassium 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 foam which
  9. customwas purified by column chromatography on silica eluting with dichloromethane
  10. additioncontaining methanol (5%)
  11. concentrationconcentrated in vacuo
  12. customto give a gum which
  13. customwas crystallised from acetonitrile

出典と根拠

ORDレコード
ord-373af05fa05342b88789b4e63b48caab
出典データセット
uspto-grants-1999_08
特許番号
US05932594

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