Potassium Carbonate → 3-(R)-(1-cyano-1,1-diphenylmethyl)-1-(2-phenoxyethyl)piperidine

HRID 21400

反応式

HRID 21400 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].[O:22]([CH2:29][CH2:30]Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:3]([C@H:16]1[CH2:21][CH2:20][CH2:19][N:18]([CH2:30][CH2:29][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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

5

反応物 3

HCID 11430Potassium CarbonateHCID 68526Benzene, (2-bromoethoxy)-HCID 228537583-(R)-(1-cyano-1,1-diphenylmethyl)-piperidine

生成物 1

HCID 228537533-(R)-(1-cyano-1,1-diphenylmethyl)-1-(2-phenoxyethyl)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 (0.3 g), 2-phenoxyethyl bromide (0.24 g--commercially available), anhydrous potassium carbonate (0.5 g) and acetonitrile (15 ml) was heated under reflux for 5 hours. The mixture was then partitioned between dichloromethane (30 ml) and 10% aqueous potassium carbonate (30 ml), the layers separated, and the aqueous layer extracted with dichloromethane (2×20 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give a gum which was purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 2%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a gum, yield 0.254 g.

後処理

  1. temperatureunder reflux for 5 hours
  2. customThe mixture was then partitioned between dichloromethane (30 ml) and 10% aqueous potassium carbonate (30 ml)
  3. customthe layers separated
  4. extractionthe aqueous layer extracted with dichloromethane (2×20 ml)
  5. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give a gum which
  8. customwas purified by column chromatography on silica eluting with dichloromethane
  9. additioncontaining methanol (0% up to 2%)
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ea33f5fb19be4a2b81c7fb2b7aa97c11
出典データセット
uspto-grants-1995_06
特許番号
US05422358

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