HCID 21546025, compound → HCID 21546050, compound

HRID 1606229Notes

Reaction equation

HRID 1606229 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]=[C:16]([O:18]CC2C=CC=CC=2)[CH:15]=[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]=[C:16]([OH:18])[CH:15]=[C:14]([OH:26])[CH:13]=1

Participants

6

Reactant 2

HCID 21546025HCID 21546025, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21546050HCID 21546050, compoundYield 63.7%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

1.4 g of α-(3,4-dimethoxyphenethylaminomethyl)-3,5-dibenzyloxybenzylalcohol hydrochloride are suspended in a mixture of 32 ml of isopropanol and 8 ml of water. 0.42 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 under reduced pressure, and the residue thus obtained is recrystallized from a mixture of methanol and ether. 0.6 g of α-(3,4-dimethoxyphenethylaminomethyl)-3,5-dihydroxybenzylalcohol hydrochloride is obtained. Yield: 63.5 % M.p. 193° - 194°C

Workup

  1. filtrationthe mixture is filtered
  2. customto remove the catalyst
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customthe residue thus obtained
  5. customis recrystallized from a mixture of methanol and ether

Sources & evidence

ORD record
ord-8a47a21212d147d2be9869902a674e20
Source dataset
uspto-grants-1976_04
Patent number
US03952021

Reaction notes

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