Ammonium Chloride → alpha-(4-Fluorophenyl)-alpha-(1-methyl-4-piperidinyl)-3-pyridinemethanol

HRID 1380243

Reaktionsgleichung

Reaktionsgleichung von HRID 1380243
Cl[CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.[Mg].[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[O:18])=[CH:13][CH:12]=1.[Cl-].[NH4+]>CC1C=CC=CC=1.O1CCCC1>[F:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([CH:2]2[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]2)([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[OH:18])=[CH:15][CH:16]=1

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 793424-chloro-N-methylpiperidineHCID 762660(4-Fluorophenyl)(pyridin-3-yl)methanoneHCID 5462224Magnesium

Produkt 1

HCID 23326054alpha-(4-Fluorophenyl)-alpha-(1-methyl-4-piperidinyl)-3-pyridinemethanolAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred and cooled Grignard-complex previously prepared starting from a mixture of 134 parts of 4-chloro-1-methylpiperidine, 25 parts of magnesium and 652.5 parts of tetrahydrofuran was added dropwise a solution of 170 parts of (4-fluorophenyl)(3-pyridinyl)methanone in 405 parts of tetrahydrofuran at a temperature between 10°-20° C. Upon completion, stirring was continued for 1 hour at room temperature and for 30 minutes at minutes at reflux. After cooling, the whole was decomposed by pouring onto a mixture of crushed ice and ammonium chloride. 270 Parts of methylbenzene were added. The organic layer was separated, dried, filtered and evaporated. The residue was boiled in acetonitrile with activated charcoal. The latter was filtered off over Hyflo and the filtrate was evaporated, yielding 240 parts (95%) of α-(4-fluorophenyl)-α-(1-methyl-4-piperidinyl)-3-pyridinemethanol as a residue (intermediate 18).

Aufarbeitung

  1. temperaturecooled Grignard-complex
  2. custompreviously prepared
  3. stirringUpon completion, stirring
  4. temperatureat reflux
  5. temperatureAfter cooling
  6. customThe organic layer was separated
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. filtrationThe latter was filtered off over Hyflo
  11. customthe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-6c0e3012146947ae9a6e5ab2b7efde83
Quelldatensatz
uspto-grants-1986_04
Patentnummer
US04581171

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