Реакция #60433

Уравнение реакции

2-cyclohept-1-enylphenylamine

bis(2-chloroethyl)amine hydrochloride

→

title compound

Выход 45.9%

1-(2-Cyclohept-1-enylphenyl)piperazine

Выход 45.9%

Растворители

1,2-dichlorobenzene

Условия реакции

Обработка

1. 1
   ДругоеDuring the reaction
2. 2
   Другоеto remove the hydrogen chloride gas in the reactor
3. 3
   Температураthe reaction mixture was air-cooled to room temperature
4. 4
   workup.ADDITIONaqueous solution of potassium carbonate, ethyl acetate and methanol were added to the reaction mixture and extraction
5. 5
   СушкаThe obtained organic layers were dried over anhydrous sodium sulfate
6. 6
   Фильтрацияthe desiccant was filtered off
7. 7
   Концентрированиеthe filtrate was concentrated under reduced pressure
8. 8
   ДругоеThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

Методика

To a solution of 2-cyclohept-1-enylphenylamine (617 mg, 3.29 mmol) in 1,2-dichlorobenzene (8 mL) was added bis(2-chloroethyl)amine hydrochloride (705 mg, 3.95 mmol), and the mixture was stirred at an external temperature of 200° C. under a nitrogen atmosphere. During the reaction, a nitrogen stream was blown into the reactor to remove the hydrogen chloride gas in the reactor. This procedure was repeated several times. After 5 hours, the reaction mixture was air-cooled to room temperature, and then aqueous solution of potassium carbonate, ethyl acetate and methanol were added to the reaction mixture and extraction was performed three times with ethyl acetate. The obtained organic layers were dried over anhydrous sodium sulfate, and then 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 387 mg of the title compound as a brown oil.

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