Water → (4-Bromophenyl)-(1-methyl-4-piperidinyl)methanone

HRID 66675

반응식

HRID 66675 반응식
Cl[CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.[Mg].[Br:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#N)=[CH:13][CH:12]=1.[Cl-].[NH4+].[OH2:21]>O1CCCC1>[Br:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]([CH:2]2[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]2)=[O:21])=[CH:13][CH:12]=1

참가 물질

7

반응물 5

HCID 962WaterHCID 12162Benzonitrile, 4-bromo-HCID 25517Ammonium ChlorideHCID 793424-chloro-N-methylpiperidineHCID 5462224Magnesium

생성물 1

HCID 20530733(4-Bromophenyl)-(1-methyl-4-piperidinyl)methanone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred and cooled (10°-15° C.) Grignard-complex, previously prepared starting from 13.5 parts of 4-chloro-1-methylpiperidine and 2.4 parts of magnesium in 68 parts of tetrahydrofuran, is added dropwise a solution of 10 parts of 4-bromobenzonitrile in 22 parts of tetrahydrofuran. Upon completion, stirring is continued for 1 hour at reflux temperature. The reaction mixture is decomposed by pouring onto a mixture of 50 parts of ammonium chloride in 250 parts of water. The product is extracted with methylbenzene. The extract is dried, filtered and evaporated. The 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, yielding 10 parts of (4-bromophenyl)-(1-methyl-4-piperidinyl)methanone as a residue.

후처리

  1. temperaturecooled (10°-15° C.) Grignard-complex
  2. custompreviously prepared
  3. stirringUpon completion, stirring
  4. temperatureat reflux temperature
  5. extractionThe product is extracted with methylbenzene
  6. customThe extract is dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is purified by column-chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  11. customThe pure fractions are collected
  12. customthe eluent is evaporated

출처 및 근거

ORD 기록
ord-93eec3e9667745f9b5688539be76b279
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04342870

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