Hydrochloric Acid → 1-(3-Methylphenyl)-2-[1-(phenylmethyl)-4-piperidinyl]ethanone hydrochloride

HRID 126862

反応式

HRID 126862 の反応式
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[CH:4]=1.[C:10]1([CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([CH2:23][C:24]#N)[CH2:19][CH2:18]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl-:26].[NH4+].Cl.CC([OH:32])C>O(CC)CC>[ClH:26].[CH3:9][C:5]1[CH:4]=[C:3]([C:24](=[O:32])[CH2:23][CH:20]2[CH2:21][CH2:22][N:17]([CH2:16][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:18][CH2:19]2)[CH:8]=[CH:7][CH:6]=1

参加物

8

反応物 6

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 115603-BromotolueneHCID 25517Ammonium ChlorideHCID 5624991-Benzylpiperidine-4-acetonitrileHCID 5462224Magnesium

生成物 1

HCID 202880461-(3-Methylphenyl)-2-[1-(phenylmethyl)-4-piperidinyl]ethanone hydrochloride収率 71%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

To a stirred and refluxing Grignard-complex, previously prepared starting from 3.65 parts of magnesium, 26 parts of 1-bromo-3-methylbenzene and 70 parts of 1,1'-oxybisethane, is added dropwise a solution of 21.4 parts of 1-(phenylmethyl)-4-piperidineacetonitrile in 70 parts of 1,1'-oxybisethane. Upon completion, stirring is continued for 4 hours at reflux temperature. The reaction mixture is cooled in and ice-bath and decomposed by the addition of a saturated ammonium chloride solution. The layers are separated and the aqueous phase is extracted twice with 1,1'-oxybisethane. The combined organic phases are dried, filtered and evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The oily residue is stirred in 2,2'-oxybispropane with activated charcoal. The latter is filtered off till a clear filtrate is obtained. The filtrate is acidified with 2 -propanol saturated with hydrogen chloride. The whole is evaporated and the residue is crystallized from warm 4-methyl-2-pentanone, yielding 24.5 parts (71%) of 1-(3-methylphenyl)-2-[1-(phenylmethyl)-4-piperidinyl]ethanone hydrochloride; mp. 165.8° C.

後処理

  1. temperaturerefluxing Grignard-complex
  2. custompreviously prepared
  3. stirringUpon completion, stirring
  4. temperatureat reflux temperature
  5. temperatureThe reaction mixture is cooled in and ice-bath
  6. customThe layers are separated
  7. extractionthe aqueous phase is extracted twice with 1,1'-oxybisethane
  8. customThe combined organic phases are dried
  9. filtrationfiltered
  10. customevaporated
  11. customThe oily residue is purified by column-chromatography over silica gel using
  12. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  13. customThe pure fractions are collected
  14. customthe eluent is evaporated
  15. stirringThe oily residue is stirred in 2,2'-oxybispropane with activated charcoal
  16. filtrationThe latter is filtered off till a clear filtrate
  17. customis obtained
  18. customThe whole is evaporated
  19. customthe residue is crystallized
  20. temperaturefrom warm 4-methyl-2-pentanone

出典と根拠

ORDレコード
ord-36ef77958bac493c8045e8d554f0948c
出典データセット
uspto-grants-1981_03
特許番号
US04254127

関連ノート

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