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

HRID 66675

Reaktionsgleichung

Reaktionsgleichung von HRID 66675
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

Komponenten

7

Edukt 5

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-93eec3e9667745f9b5688539be76b279
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04342870

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