Reaktion #60499

Reaktionsgleichung

4,5-dimethoxy-2-(3,3,5,5-tetramethylcyclohexyl)phenylamine

bis(2-chloroethyl)amine hydrochloride

→

title compound

1-[4,5-Dimethoxy-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine

Lösungsmittel

1,2-dichlorobenzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeDuring the reaction, nitrogen gas
2. 2
   Sonstigeto remove the excess hydrogen chloride gas from the reactor
3. 3
   TemperaturThe reaction mixture was cooled to room temperature
4. 4
   workup.ADDITIONsaturated aqueous solution of sodium hydrogencarbonate was added
5. 5
   Extraktionextraction
6. 6
   ExtraktionThe aqueous layer was again extracted with chloroform
7. 7
   Waschenwashed with brine
8. 8
   Trocknendried over anhydrous magnesium sulfate
9. 9
   FiltrationThe desiccant was filtered off
10. 10
    Einengenthe filtrate was concentrated under reduced pressure
11. 11
    SonstigeThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

Vorschrift

A mixture of the crude product of 4,5-dimethoxy-2-(3,3,5,5-tetramethylcyclohexyl)phenylamine produced in Example (87c), bis(2-chloroethyl)amine hydrochloride (700 mg, 3.91 mmol) and 1,2-dichlorobenzene (10 ml) was stirred for 2 hours at an external temperature of 220° C. During the reaction, nitrogen gas was blown in several times to remove the excess hydrogen chloride gas from the reactor. The reaction mixture was cooled to room temperature, saturated aqueous solution of sodium hydrogencarbonate was added and extraction was performed with chloroform. The aqueous layer was again extracted with chloroform, and the organic layers were combined, washed with brine and then dried over anhydrous magnesium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 490 mg of the title compound as a brown oil.

Quelle