Reaktion #1993604

Reaktionsgleichung

Chlorosulfonic acid

N-(3-hydroxypropyl)-N-[2-(4-methoxyphenylmethylene)cyclohexyl]amine

→

(±)-(E)-1-[2-[(4-methoxyphenyl)methylene]cyclohexyl]azetidine

Lösungsmittel

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwith cooling
2. 2
   workup.WAITat room temperature for 2 hr to ensure complete
3. 3
   Sonstigereaction
4. 4
   FiltrationThe resulting suspension was filtered
5. 5
   Waschenthe solid washed with diethyl ether
6. 6
   workup.ADDITIONThe solid was added to a cold solution of 6.5 g of sodium hydroxide in 50 ml of water
7. 7
   Temperaturthe mixture was heated at 95° C. for 2 hr
8. 8
   Temperaturcooled in ice, saturated with solid sodium hydroxide
9. 9
   Extraktionextracted with chloroform
10. 10
    ExtraktionThe chloroform extract
11. 11
    Trocknenwas dried with magnesium sulfate
12. 12
    Sonstigeevaporated
13. 13
    SonstigeThe residue was chromatographed on a Merck silica gel size C column
14. 14
    workup.ADDITIONcontaining 1% v/v ammonium hydroxide solution mixture as eluent
15. 15
    WaschenElution of the residue loaded column with 560 ml of this mixture
16. 16
    Sonstigegave no material

Vorschrift

Chlorosulfonic acid was added dropwise during 7 min to a solution of N-(3-hydroxypropyl)-N-[2-(4-methoxyphenylmethylene)cyclohexyl]amine, 5 g (0.017 mole) in 325 ml of diethyl ether keeping the temperature at about 3° C. with cooling. The mixture was then stirred at this 3° C. temperature for 30 min and then at room temperature for 2 hr to ensure complete reaction. The resulting suspension was filtered and the solid washed with diethyl ether. The solid was added to a cold solution of 6.5 g of sodium hydroxide in 50 ml of water and the mixture was heated at 95° C. for 2 hr, then cooled in ice, saturated with solid sodium hydroxide and extracted with chloroform. The chloroform extract was dried with magnesium sulfate and evaporated. The residue was chromatographed on a Merck silica gel size C column using an 8% v/v methanol in chloroform solution containing 1% v/v ammonium hydroxide solution mixture as eluent. Elution of the residue loaded column with 560 ml of this mixture gave no material. The next 500 ml gave 0.41 g of (±)-(E)-1-[2-[(4-methoxyphenyl)methylene]cyclohexyl]azetidine as an oil. The NMR was consistent for this named product. A crystalline p-toluenesulfonate salt was prepared, mp 114°-115° C.

Quelle