Реакция #60448

Уравнение реакции

2-(3,3,4,4-tetramethylcyclopent-1-enyl)phenylamine

bis(2-chloroethyl)amine hydrochloride

→

title compound

Выход 50.9%

1-[2-(3,3,4,4-Tetramethylcyclopent-1-enyl)phenyl]piperazine

Выход 50.9%

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
5. 5
   Экстракцияextraction
6. 6
   СушкаThe obtained organic layers were dried over anhydrous sodium sulfate
7. 7
   ФильтрацияThe desiccant was filtered off
8. 8
   Концентрированиеthe filtrate was concentrated under reduced pressure
9. 9
   ДругоеThe obtained residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

Методика

A mixture of 2-(3,3,4,4-tetramethylcyclopent-1-enyl)phenylamine (331 mg, 1.54 mmol) produced in Example (54c), 1,2-dichlorobenzene (4.7 mL) and bis(2-chloroethyl)amine hydrochloride (330 mg, 1.85 mmol) was stirred for 9 hours at an external temperature of 200° C. under a nitrogen atmosphere. During the reaction, a nitrogen stream was blown into the reactor several times to remove the hydrogen chloride gas in the reactor. The reaction mixture was air-cooled to room temperature, and then aqueous solution of potassium carbonate, ethyl acetate and methanol were added and extraction was performed three times with ethyl acetate. The obtained organic layers were dried over anhydrous sodium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The obtained residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 223 mg of the title compound as a brown oil.

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