Acetaldehyde → 1-(3,4-Methylenedioxyphenyl)-2-ethylaminoethanol hydrochloride

HRID 26001Notes

Reaction equation

HRID 26001 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.[CH:15](=O)[CH3:16].[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][CH2:15][CH3:16])=[CH:5][C:4]=2[O:3]1

Participants

6

Reactant 3

HCID 177AcetaldehydeHCID 14318106HCID 14318106, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 213260981-(3,4-Methylenedioxyphenyl)-2-ethylaminoethanol hydrochloride

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

18 g. of 1-(3,4-methylenedioxyphenyl)-2-aminoethanol hydrochloride are dissolved in 300 ml. of ethanol and 50 ml. of 80% aqueous solution of acetaldehyde. To the resulting solution are added 0.5 g. of extended Raney nickel and the mixture is heated at 70° C. in an atmosphere of hydrogen in a 1 liter-autoclave. After the absorption of hydrogen is complete, the mixture is cooled. Then the catalyst is filtered off and the filtrate is concentrated to dryness. Upon recrystallization of the crude crystalline residue from isopropyl alcohol, 12.5 g. of 1-(3,4-methylenedioxyphenyl)-2-ethylaminoethanol hydrochloride are obtained as white needles.

Workup

  1. additionTo the resulting solution are added 0.5 g
  2. customAfter the absorption of hydrogen
  3. temperaturethe mixture is cooled
  4. filtrationThen the catalyst is filtered off
  5. concentrationthe filtrate is concentrated to dryness
  6. customUpon recrystallization of the crude crystalline residue from isopropyl alcohol, 12.5 g

Sources & evidence

ORD record
ord-551580bfd33349668c8de1563891ed34
Source dataset
uspto-grants-1979_04
Patent number
US04147799

Reaction notes

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