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

HRID 348538

반응식

HRID 348538 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 887Methanol용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-3c13606a6f0e4b3a8fc649fc7bd67477
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176316B2

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