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

HRID 371159
ノート
印刷プレビュー

反応式

HRID 371159 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 5234Sodium ChlorideHCID 7841Allyl bromide2 回HCID 11430Potassium CarbonateHCID 70413103Cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol

生成物 1

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

試薬・触媒・溶媒 1

HCID 702
Ethanol
溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2ed4053db0bb40a18647370a4467efbd
出典データセット
uspto-grants-1985_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04529732

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート