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Sodium Chloride → N-(2-Propenyl)-cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol

HRID 371159
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HRID 371159 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:10]=1[C@H:24]1[CH2:29][C@@H:28]([OH:30])[CH2:27][CH2:26][NH:25]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:32][CH:33]=[CH2:34].C(=O)([O-])[O-].[K+].[K+].[Cl-].[Na+]>C(O)C>[CH2:34]([N:25]1[CH2:26][CH2:27][C@H:28]([OH:30])[CH2:29][C@@H:24]1[C:10]1[CH:11]=[CH:12][C:13]([C:15]([CH3:22])([CH3:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:33]=[CH2:32]
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HCID 5234Sodium ChlorideHCID 7841Allyl bromide2회HCID 11430Potassium CarbonateHCID 70413103Cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol

생성물 1

HCID 70490735N-(2-Propenyl)-cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol수율 62.6%

시약·촉매·용매 1

HCID 702
Ethanol
용매

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온도
25 °C

실험 절차

A mixture of 778 mg (1.90 mmole) of cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol, 160 microliters (1.84 mmole) of 1-bromo-2-propene and 300 mg (2.17 mmole) of potassium carbonate in 10 ml ethanol is stirred at 25° C. for 20.5 hours. An additional 4 microliters of 1-bromo-2-propene is added to the reaction and stirring continued for 7 hours. The reaction mixture is then added to 50 ml saturated sodium chloride and extracted with 250 ml ethyl ether. The ether extract is dried over magnesium sulfate and the solvent is evaporated. The resulting oil is purified via column chromatography on 28 g of silica gel eluted in 7 ml fractions with 1:3 methanol/ethyl ether to yield (fractions 10-35) 518 mg (61%) of the title compound as an oil.

후처리

  1. stirringstirring
  2. waitcontinued for 7 hours
  3. extractionextracted with 250 ml ethyl ether
  4. extractionThe ether extract
  5. dry with materialis dried over magnesium sulfate
  6. customthe solvent is evaporated
  7. customThe resulting oil is purified via column chromatography on 28 g of silica gel
  8. washeluted in 7 ml fractions with 1:3 methanol/ethyl ether

출처 및 근거

ORD 기록
ord-2ed4053db0bb40a18647370a4467efbd
출처 데이터셋
uspto-grants-1985_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04529732

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