反応 #60469

反応方程式

sodium hydrogencarbonate

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

1,2-dichlorobenzene

bis(2-chloroethyl)amine hydrochloride

→

title compound

収率 73.5%

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

収率 73.5%

溶媒

chloroform

反応条件

後処理

1. 1
   その他During the reaction
2. 2
   温度The reaction mixture was cooled to room temperature
3. 3
   その他the filtrate obtained by filtration through Celite
4. 4
   抽出was extracted with chloroform
5. 5
   洗浄The separated organic layer was washed with brine
6. 6
   乾燥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 resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

実験手順

To a mixture of 3-methyl-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenylamine (663 mg, 2.72 mmol) produced in Example (71b) and 1,2-dichlorobenzene (3 mL) was added bis(2-chloroethyl)amine hydrochloride (632 mg, 3.54 mmol), followed by stirring for 5 hours and 50 minutes at an external temperature of 200° C. under a nitrogen atmosphere. During the reaction, a nitrogen stream was passed through the reactor several times. The reaction mixture was cooled to room temperature, chloroform and saturated solution of sodium hydrogencarbonate were added, and the filtrate obtained by filtration through Celite was extracted with chloroform. The separated organic layer was washed with brine and then 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/hexane) to give 625 mg of the title compound as a yellow solid.

出典