Isopropylamine → 1-(3,4-Methylenedioxyphenyl)-2-isopropylaminoethanol hydrochloride

HRID 26000Notes

Reaction equation

HRID 26000 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]([OH:13])[CH2:11][Cl:12])=[CH:4][C:3]=2[O:2]1.[CH:14]([NH2:17])([CH3:16])[CH3:15]>C(O)C>[ClH:12].[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]([OH:13])[CH2:11][NH:17][CH:14]([CH3:16])[CH3:15])=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 224917731-(3,4-Methylenedioxyphenyl)-2-chloroethanol

Product 1

HCID 123482941-(3,4-Methylenedioxyphenyl)-2-isopropylaminoethanol hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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.

Workup

  1. temperatureAfter cooling
  2. customthe ethanol and excess amine are removed by distillation under reduced pressure
  3. extractionThe residue is extracted with 100 ml
  4. washof 1N HCl and the extract is washed twice with 50 ml
  5. extractionThe hydrochloric acid extract
  6. extractionthe liberated oil is extracted with ether
  7. extractionThe ether extract
  8. customis dried
  9. additionan etherial hydrochloric acid solution is added
  10. filtrationis filtered
  11. customdried
  12. customUpon recrystallization of the crude crystals from isopropyl alcohol, 6.4 g

Sources & evidence

ORD record
ord-68adba173cd44fdbb7ecad9cbd0a1ec0
Source dataset
uspto-grants-1979_04
Patent number
US04147799

Reaction notes

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