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Thiophene → HCID 13094234、化合物

HRID 1164365
ノート
印刷プレビュー

反応式

HRID 1164365 の反応式
S1C=CC=C1.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2([C:20]#[N:21])[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]2)=[C:9]([CH3:22])[CH:8]=1.Cl.[C:24]1([C:30]2([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])(=O)C.[Na+].[H][H]>[Pd].C(O)C>[C:20]([C:13]1([C:10]2[CH:11]=[CH:12][C:7]([F:6])=[CH:8][C:9]=2[CH3:22])[CH2:18][CH2:17][CH:16]([N:33]2[CH2:32][CH2:31][C:30]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:35][CH2:34]2)[CH2:15][CH2:14]1)#[N:21]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 8030ThiopheneHCID 517045Sodium AcetateHCID 205117981-(4-Fluoro-2-methylphenyl)-4-oxocyclohexanecarbonitrileHCID 53444519Ethyl 4-phenylpiperidine-4-carboxylate--hydrogen chloride (1/1)HCID 178418361HCID 178418361、化合物

生成物 1

HCID 13094234HCID 13094234、化合物収率 33.4%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒2 回

実験手順

To 1 part of a solution of 2 parts of thiophene in 40 parts of ethanol are added 4.7 parts of 1-(4-fluoro-2-methylphenyl)-4-oxocyclohexanecarbonitrile, 5.4 parts of ethyl 4-phenyl-4-piperidinecarboxylate hydrochloride, 2 parts of sodium acetate and 120 parts of ethanol. The whole is hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charocal catalyst 10%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off over Hyflo and the filtrate is evaporated. From the residue, the free base is liberated in the conventional manner with ammonium hydroxide and the product is extracted with dichloromethane. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and ethanol (98.5:1.5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from ethanol, yielding 3 parts (33.4%) of ethyl 1-[4-cyano-4-(4-fluoro-2-methylphenyl)cyclohexyl]-4 -phenyl-4-piperidinecarboxylate; mp. 135.2° C.

後処理

  1. filtrationthe catalyst is filtered off over Hyflo
  2. customthe filtrate is evaporated
  3. extractionthe product is extracted with dichloromethane
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and ethanol (98.5:1.5 by volume) as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. customThe residue is crystallized from ethanol

出典と根拠

ORDレコード
ord-b99139ca3569457cb1096477051642aa
出典データセット
uspto-grants-1983_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04369184

反応ノート

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