HCID 54500163, compound → HCID 54186283, compound

HRID 1462370Notes

Reaction equation

HRID 1462370 reaction equation
C([O:8][C:9]1[CH:31]=[CH:30][C:12]([CH:13]([OH:29])[CH2:14][NH:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:27])[NH2:26])=[C:21]([OH:28])[CH:20]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>O1CCOCC1.[Pd]>[C:25]([C:22]1[CH:23]=[CH:24][C:19]([O:18][CH2:17][CH2:16][NH:15][CH2:14][CH:13]([OH:29])[C:12]2[CH:30]=[CH:31][C:9]([OH:8])=[CH:10][CH:11]=2)=[CH:20][C:21]=1[OH:28])(=[O:27])[NH2:26]

Participants

5

Reactant 2

HCID 54500163HCID 54500163, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54186283HCID 54186283, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 8.7 g of 4-benzyloxy-α-[N-[2-(4-carbamoyl-3-hydroxy-phenoxy)-ethyl]-aminomethyl]-benzyl alcohol in 100 ml of dioxan is hydrogenated under normal conditions with the addition of 2 g of palladium-on-charcoal catalyst (5%) until 1 equivalent of hydrogen has been taken up. The product which has precipitated is brought into solution after adding 200 ml of methanol, by warming, the catalyst is filtered off and the filtrate is evaporated. Recrystallisation of the residue from isopropanol yields crystalline α-[N-[2-(4-carbamoyl-3-hydroxy-phenoxy)-ethyl]-aminomethyl]-4-hydroxybenzyl alcohol with a melting point of 181°-182°.

Workup

  1. customThe product which has precipitated
  2. additionafter adding 200 ml of methanol
  3. temperatureby warming
  4. filtrationthe catalyst is filtered off
  5. customthe filtrate is evaporated
  6. customRecrystallisation of the residue from isopropanol

Sources & evidence

ORD record
ord-43758d9fb61b4c608c60fa57462c4dfd
Source dataset
uspto-grants-1984_07
Patent number
US04460580

Reaction notes

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