HCID 69766304, compound → HCID 10404453, compound

HRID 966106Notes

Reaction equation

HRID 966106 reaction equation
Cl.[OH:2][C:3]1[C:4]([O:24][CH3:25])=[C:5]([C:10](=[O:23])[CH2:11][NH:12][C:13]([CH3:22])([CH3:21])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:7][C:8]=1[OH:9]>CO.[Pt](=O)=O>[CH3:22][C:13]([NH:12][CH2:11][CH:10]([C:5]1[C:4]([O:24][CH3:25])=[C:3]([OH:2])[C:8]([OH:9])=[CH:7][CH:6]=1)[OH:23])([CH3:21])[CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 1

HCID 69766304HCID 69766304, compound

Product 1

HCID 10404453HCID 10404453, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

10 g of 1-(3,4-dihydroxy-2-methoxyphenyl)-2-(1,1-dimethyl-2-phenylethylamino)ethanone hydrochloride is hydrogenated with 0.5 g of platinum(IV) oxide in 200 mL methanol. The catalyst is suction filtered and the solvent is distilled off under reduced pressure. The residue remaining is dissolved in 200 mL acetonitrile, combined with 5 g of sodium benzoate and refluxed for 15 minutes. After the excess sodium benzoate has been filtered off, the product which crystallizes out of the filtrate is filtered off and washed with acetonitrile and diethyl ether. Yield: 64.5% (benzoate); melting point: 149° C.-150° C.

Workup

  1. filtrationfiltered
  2. distillationthe solvent is distilled off under reduced pressure
  3. dissolutionThe residue remaining is dissolved in 200 mL acetonitrile
  4. temperaturerefluxed for 15 minutes
  5. filtrationAfter the excess sodium benzoate has been filtered off
  6. customthe product which crystallizes out of the filtrate
  7. filtrationis filtered off
  8. washwashed with acetonitrile and diethyl ether

Sources & evidence

ORD record
ord-8914d004eec047e09517829430d632a7
Source dataset
uspto-grants-2005_10
Patent number
US06951888B2

Reaction notes

Loading…