Reaction #54280

Reaction equation

1-(3,4-methylenedioxyphenyl)-2-chloroethanol

ethylamine

→

1-(3,4-methylenedioxyphenyl)-2-ethylaminoethanol hydrochloride

Solvents

ethanol

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   workup.DISTILLATIONthe ethanol and excess ethylamine are distilled off under reduced pressure
3. 3
   ExtractionThe residue is extracted with 100 ml
4. 4
   Washof 1N HCl and the extract is washed twice with 100 ml
5. 5
   ExtractionThe hydrochloric acid extract solution
6. 6
   Extractionthe liberated oil is extracted with ether
7. 7
   ExtractionThe ether extract
8. 8
   Otheris dried
9. 9
   workup.ADDITIONan etherial hydrochloric acid solution is added
10. 10
    Filtrationare filtered off
11. 11
    Washwashed with ether
12. 12
    OtherUpon recrystallization from isopropyl alcohol 7.8 g

Procedure

19.5 g. of 1-(3,4-methylenedioxyphenyl)-2-chloroethanol are added to a solution of 170 g. of ethylamine in 200 ml. of cooled ethanol and the mixture is heated at 80° C. for 8 hours in an autoclave. After cooling, the ethanol and excess ethylamine are distilled off under reduced pressure. The residue is extracted with 100 ml. of 1N HCl and the extract is washed twice with 100 ml. of ether. The hydrochloric acid extract solution is made basic with 1N caustic soda and the liberated oil is extracted with ether. The ether extract is dried and an etherial hydrochloric acid solution is added thereto. The crystals which settle out on standing are filtered off and washed with ether. Upon recrystallization from isopropyl alcohol 7.8 g. of 1-(3,4-methylenedioxyphenyl)-2-ethylaminoethanol hydrochloride are obtained.

Source