반응 #60448

반응 방정식

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

bis(2-chloroethyl)amine hydrochloride

→

title compound

수율 50.9%

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

수율 50.9%

용매

1,2-dichlorobenzene

반응 조건

후처리

1. 1
   기타During the reaction
2. 2
   기타to remove the hydrogen chloride gas in the reactor
3. 3
   온도The reaction mixture was air-cooled to room temperature
4. 4
   workup.ADDITIONaqueous solution of potassium carbonate, ethyl acetate and methanol were added
5. 5
   추출extraction
6. 6
   건조The obtained organic layers were dried over anhydrous sodium sulfate
7. 7
   여과The desiccant was filtered off
8. 8
   농축the filtrate was concentrated under reduced pressure
9. 9
   기타The obtained residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

실험 절차

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.

출처