Reaktion #60448

Reaktionsgleichung

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

bis(2-chloroethyl)amine hydrochloride

→

title compound

Ausbeute 50.9%

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

Ausbeute 50.9%

Lösungsmittel

1,2-dichlorobenzene

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle