تفاعل #60516

معادلة التفاعل

3-fluoro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenylamine

bis(2-chloroethyl)amine hydrochloride

→

title compound

المردود 26.8%

1-[3-Fluoro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenyl]piperazine

المردود 26.8%

المذيبات

1,2-dichlorobenzene

ظروف التفاعل

المعالجة

1. 1
   أخرىDuring the reaction
2. 2
   أخرىto remove the hydrogen chloride gas
3. 3
   درجة الحرارةAfter cooling the reaction mixture to room temperature
4. 4
   workup.ADDITIONethyl acetate, tetrahydrofuran, methanol, saturated aqueous solution of sodium carbonate and water were added
5. 5
   أخرىfor partition between oil and water
6. 6
   استخلاصThe aqueous layer was further extracted with ethyl acetate
7. 7
   تجفيفthe combined organic layer was dried over anhydrous sodium sulfate
8. 8
   ترشيحThe desiccant was filtered off
9. 9
   تركيزthe filtrate was concentrated under reduced pressure
10. 10
    أخرىThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

الإجراء التجريبي

To a solution of 3-fluoro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenylamine (623 mg, 2.52 mmol) produced in Example (97c) in 1,2-dichlorobenzene (7 mL) was added bis(2-chloroethyl)amine hydrochloride (560 mg, 3.14 mmol), followed by reflux for 5 hours at an external temperature of 200° C. under a nitrogen atmosphere. During the reaction, a nitrogen stream was circulated into the reactor several times to remove the hydrogen chloride gas. After cooling the reaction mixture to room temperature, ethyl acetate, tetrahydrofuran, methanol, saturated aqueous solution of sodium carbonate and water were added for partition between oil and water. The aqueous layer was further extracted with ethyl acetate, and the combined organic layer was dried over anhydrous sodium 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 214 mg of the title compound as a light brown oil.

المصدر