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

HRID 25998Notes

Reaction equation

HRID 25998 reaction equation
[ClH:1].[CH2:2]1[O:10][C:9]2[CH:8]=[CH:7][C:6]([CH:11]([OH:14])[CH2:12][NH2:13])=[CH:5][C:4]=2[O:3]1.[CH3:15][C:16]([CH3:18])=O.[H][H]>[Ni].C(O)C>[ClH:1].[CH2:2]1[O:10][C:9]2[CH:8]=[CH:7][C:6]([CH:11]([OH:14])[CH2:12][NH:13][CH:16]([CH3:18])[CH3:15])=[CH:5][C:4]=2[O:3]1

Participants

6

Reactant 3

HCID 180AcetoneHCID 14318106HCID 14318106, compoundHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

18.1 g. of 1-(3,4-methylenedioxyphenyl)-2-aminoethanol hydrochloride are dissolved in 20 ml. of acetone and 300 ml. of ethanol. To the resulting solution are added 10 g. of extended Raney nickel and the mixture is heated and stirred at 70° C. in an atmosphere of hydrogen in an autoclave. After the absorption of hydrogen is complete, the catalyst is filtered off and the filtrate is concentrated to dryness. Upon recrystallization of the crude crystalline residue from isopropyl alcohol, 14.4 g. of 1-(3,4-methylenedioxyphenyl)-2-isopropylaminoethanol hydrochloride are obtained as white needles.

Workup

  1. additionTo the resulting solution are added 10 g
  2. customAfter the absorption of hydrogen
  3. filtrationthe catalyst is filtered off
  4. concentrationthe filtrate is concentrated to dryness
  5. customUpon recrystallization of the crude crystalline residue from isopropyl alcohol, 14.4 g

Sources & evidence

ORD record
ord-b33b40df03fe40cfb2721b30df95839f
Source dataset
uspto-grants-1979_04
Patent number
US04147799

Reaction notes

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