Sodium Carbonate → (+/-)-1-(cis-2-Phenyl-cyclohexyl)-piperidin-4-one

HRID 348538

反応式

HRID 348538 の反応式
[C:1]1([C@H:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]2[N:13]2[CH2:22][CH2:21][C:16]3(OCC[O:17]3)[CH2:15][CH2:14]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+]>CO.Cl>[C:1]1([C@H:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]2[N:13]2[CH2:22][CH2:21][C:16](=[O:17])[CH2:15][CH2:14]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 2

HCID 10340Sodium CarbonateHCID 69486512(+/-)-8-(cis 2-Phenyl-cyclohexyl)-1,4-dioxa-8-aza-spiro[4,5]decane

生成物 1

HCID 69486592(+/-)-1-(cis-2-Phenyl-cyclohexyl)-piperidin-4-one収率 75.3%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 887Methanol溶媒

実験手順

A solution of (+/−)-8-(cis 2-phenyl-cyclohexyl)-1,4-dioxa-8-aza-spiro[4,5]decane (44.8 g) in MeOH (100 ml) and 6N HCl (445 ml) was heated to reflux for 16 h. The reaction mixture was then made basic with solid sodium carbonate, extracted with dichloromethane, dried over sodium sulphate, filtered and evaporated. The crude product was purified by flash chromatography over silica gel with n-heptane as eluent. (+/−)-1-(cis-2-phenyl-cyclohexyl)-piperidin-4-one (28.8 g, 75%) was obtained as a sticky yellow oil, MS (ISP): m/e=258.3 (M+H+).

後処理

  1. temperatureto reflux for 16 h
  2. extractionextracted with dichloromethane
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by flash chromatography over silica gel with n-heptane as eluent

出典と根拠

ORDレコード
ord-3c13606a6f0e4b3a8fc649fc7bd67477
出典データセット
uspto-grants-2007_02
特許番号
US07176316B2

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