反応 #60516

反応方程式

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

bis(2-chloroethyl)amine hydrochloride

→

title compound

収率 26.8%

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

収率 26.8%

溶媒

1,2-dichlorobenzene

反応条件

後処理

1. 1
   その他During the reaction
2. 2
   その他to remove the hydrogen chloride gas
3. 3
   温度After 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
   その他for partition between oil and water
6. 6
   抽出The aqueous layer was further extracted with ethyl acetate
7. 7
   乾燥the combined organic layer was dried over anhydrous sodium sulfate
8. 8
   ろ過The desiccant was filtered off
9. 9
   濃縮the filtrate was concentrated under reduced pressure
10. 10
    その他The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

実験手順

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.

出典