反応 #60448

反応方程式

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

bis(2-chloroethyl)amine hydrochloride

→

title compound

収率 50.9%

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

収率 50.9%

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 in the reactor
3. 3
   温度The reaction mixture was air-cooled to room temperature
4. 4
   workup.ADDITIONaqueous solution of potassium carbonate, ethyl acetate and methanol were added
5. 5
   抽出extraction
6. 6
   乾燥The obtained organic layers were dried over anhydrous sodium sulfate
7. 7
   ろ過The desiccant was filtered off
8. 8
   濃縮the filtrate was concentrated under reduced pressure
9. 9
   その他The obtained residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

実験手順

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.

出典