4-(2-(Benzyl(methyl)amino)-1-hydroxyethyl)benzene-1,2-diol → (+-)-Adrenaline

HRID 324713

Reaction equation

HRID 324713 reaction equation
[CH2:1]([N:8]([CH2:10][CH:11]([C:13]1[CH:20]=[CH:19][C:17]([OH:18])=[C:15]([OH:16])[CH:14]=1)[OH:12])C)C1C=CC=CC=1.[H][H]>O.S(=O)(=O)(O)O.[Pd]>[CH3:1][NH:8][CH2:10][CH:11]([C:13]1[CH:20]=[CH:19][C:17]([OH:18])=[C:15]([OH:16])[CH:14]=1)[OH:12]

Participants

6

Reactant 2

HCID 220059034-(2-(Benzyl(methyl)amino)-1-hydroxyethyl)benzene-1,2-diolHCID 178418361HCID 178418361, compound

Product 1

HCID 838(+-)-Adrenaline

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

Benzyladrenaline 2 is dissolved in about 10 ml of water and about 5 ml of 18% sulfuric acid (pH: about 5.5), about 50 mg of palladium-charcoal (10%) are added and the mixture is hydrogenated at about 60° C. under 2 bar of hydrogen pressure. It is then evaporated down to about half its volume, about 20 ml of methanol are added and the mixture is cooled. The crystalline product (adrenaline sulphate 3) is filtered off and dried.

Workup

  1. customIt is then evaporated down to about half its volume, about 20 ml of methanol
  2. additionare added
  3. temperaturethe mixture is cooled
  4. filtrationThe crystalline product (adrenaline sulphate 3) is filtered off
  5. customdried

Sources & evidence

ORD record
ord-0d5d680909424c2b8d92acfc8a968ddf
Source dataset
uspto-grants-2001_04
Patent number
US06218575B1

Linked notes

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