HCID 21546033, compound → HCID 21546028, compound

HRID 1606228Notes

Reaction equation

HRID 1606228 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:35]=[CH:36][C:37]=1[O:38][CH3:39])[CH2:7][CH2:8][NH:9][CH2:10][CH:11]([OH:34])[C:12]1[CH:17]=[CH:16][C:15]([O:18]CC2C=CC=CC=2)=[C:14]([O:26]CC2C=CC=CC=2)[CH:13]=1.[H][H]>C(O)(C)C.O.[C].[Pd]>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:35]=[CH:36][C:37]=1[O:38][CH3:39])[CH2:7][CH2:8][NH:9][CH2:10][CH:11]([OH:34])[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([OH:26])[CH:13]=1

Participants

6

Reactant 2

HCID 21546033HCID 21546033, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21546028HCID 21546028, compoundYield 104.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

3.0 g of α-(3,4-dimethoxyphenethylaminomethyl)-3,4-dibenzyloxybenzylalcohol hydrochloride are suspended in a mixture of 80 ml of isopropanol and 20 ml of water. One g of 10 % palladium-carbon is added to the solution. Then, the mixture is subjected to catalytic hydrogenation in a hydrogen atmosphere at room temperature for 1 hour under atmospheric pressure. After the reaction is completed, the mixture is filtered to remove the catalyst. The filtrate is concentrated to dryness under reduced pressure, and the residue thus obtained is recrystallized from aqueous isopropanol. 2.1 g of α-(3,4-dimethoxyphenethylaminomethyl)-3,4-dihydroxybenzylalcohol hydrochloride are obtained. Yield: 90 % M.p. 98° - 109°C (decomp.)

Workup

  1. filtrationthe mixture is filtered
  2. customto remove the catalyst
  3. concentrationThe filtrate is concentrated to dryness under reduced pressure
  4. customthe residue thus obtained
  5. customis recrystallized from aqueous isopropanol

Sources & evidence

ORD record
ord-c0c680ca751c49c9bbc2be9122f8e494
Source dataset
uspto-grants-1976_04
Patent number
US03952021

Reaction notes

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