Reaction #54278

Reaction equation

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

isopropylamine

→

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

Solvents

ethanol

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   Otherthe ethanol and excess amine are removed by distillation under reduced pressure
3. 3
   ExtractionThe residue is extracted with 100 ml
4. 4
   Washof 1N HCl and the extract is washed twice with 50 ml
5. 5
   ExtractionThe hydrochloric acid extract
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
    Filtrationis filtered
11. 11
    Otherdried
12. 12
    OtherUpon recrystallization of the crude crystals from isopropyl alcohol, 6.4 g

Procedure

20.5 g. of 1-(3,4-methylenedioxyphenyl)-2-chloroethanol are mixed with 30 g. of isopropylamine and 100 ml. of ethanol and the mixture is refluxed for 8 hours. After cooling, the ethanol and excess amine are removed by distillation under reduced pressure. The residue is extracted with 100 ml. of 1N HCl and the extract is washed twice with 50 ml. of ether. The hydrochloric acid extract 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. The crystalline hydrochloride settles out of solution and is filtered and dried. Upon recrystallization of the crude crystals from isopropyl alcohol, 6.4 g. of 1 -(3,4-methylenedioxyphenyl)-2-isopropylaminoethanol hydrochloride are obtained.

Source