Reaktion #531529

Reaktionsgleichung

sodium cyanoborohydride

3-[4-(1,1-dimethyl-heptyl)-2-hydroxyphenyl]-1,2,5,6-tetrahydropyridine

acetonitrile

formaldehyde

→

title compound

3-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-1-N-methyl-1,2,5,6-tetrahydropyridine

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 25° C.
2. 2
   Temperaturto warm to 25° C. over a one hour period while the pH
3. 3
   SonstigeThe reaction mixture is evaporated
4. 4
   Extraktionextracted with 200 ml
5. 5
   ExtraktionThe organic extract
6. 6
   Trocknenis dried over magnesium sulfate
7. 7
   Sonstigeevaporated
8. 8
   SonstigeThe residue is crystallized from ether-pentane
9. 9
   Sonstigeto yield 350 mg

Vorschrift

To a 25° C. solution of 1.0 g. (3.32 mmoles) of 3-[4-(1,1-dimethyl-heptyl)-2-hydroxyphenyl]-1,2,5,6-tetrahydropyridine in 15 ml. of acetonitrile is added 1.32 ml. (17.6 mmoles) of 37% formaldehyde solution. After stirring for one hour the reaction is cooled to 0° C. and 332 mg. (5.3 mmole) of sodium cyanoborohydride added. The reaction mixture is allowed to warm to 25° C. over a one hour period while the pH is maintained at 7 by the addition of acetic acid. The reaction mixture is evaporated, made basic with 2 N potassium hydroxyide and extracted with 200 ml. of dichloromethane. The organic extract is dried over magnesium sulfate and evaporated. The residue is crystallized from ether-pentane to yield 350 mg. of the title compound.

Quelle