HCID 10461505, compound → HCID 54514397, compound

HRID 1462373Notes

Reaction equation

HRID 1462373 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:43]=[CH:44][C:45]=1[OH:46])[O:7][CH2:8][CH2:9][N:10](CC1C=CC=CC=1)[CH2:11][CH:12]([C:14]1[CH:19]=[C:18]([O:20]CC2C=CC=CC=2)[CH:17]=[C:16]([O:28]CC2C=CC=CC=2)[CH:15]=1)[OH:13])(=[O:3])[NH2:2].[H][H]>CO.[Pd]>[C:1]([C:4]1[CH:5]=[C:6]([CH:43]=[CH:44][C:45]=1[OH:46])[O:7][CH2:8][CH2:9][NH:10][CH2:11][CH:12]([OH:13])[C:14]1[CH:19]=[C:18]([OH:20])[CH:17]=[C:16]([OH:28])[CH:15]=1)(=[O:3])[NH2:2]

Participants

5

Reactant 2

HCID 10461505HCID 10461505, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54514397HCID 54514397, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 31 g of crude N-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethyl]-N-[2-(3,5-dibenzyloxyphenyl)-2-hydroxy-ethyl]-benzylamine in 300 ml of methanol is hydrogenated under normal conditions over 6 g of palladium-on-charcoal catalyst (5%) until 3 mol equivalents of hydrogen have been taken up. The catalyst is filtered off, the filtrate is evaporated and the residue is dissolved in 200 ml of isopropanol. Filtering through silica gel and evaporating the filtrate yields α-[N-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethyl]aminomethyl]-3,5-dihydroxy-benzyl alcohol in the form of a brownish foam. After recrystallisation from ethylacetate/methanol the compound is obtained in pure state with a melting point of 203°-205°, and contains 1/4 mol of crystal-water. The compound is characterised by the following signals in the proton nuclear magnetic resonance spectrum in hexadeuterodimethylsulfoxide as the solvent:

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. dissolutionthe residue is dissolved in 200 ml of isopropanol
  4. filtrationFiltering through silica gel
  5. customevaporating the filtrate

Sources & evidence

ORD record
ord-1e849d3b9ea14ee0b59637a364f33d88
Source dataset
uspto-grants-1984_07
Patent number
US04460580

Reaction notes

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