HCID 21333249, compound → HCID 21333201, compound

HRID 1390651Notes

Reaction equation

HRID 1390651 reaction equation
C([N:8]([CH2:21][CH:22]([OH:32])[CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31])[CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:20])[NH2:19])=[CH:14][N:13]=1)C1C=CC=CC=1.[H][H]>O1CCOCC1.[Pd]>[C:18]([C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][NH:8][CH2:21][CH:22]([OH:32])[CH2:23][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:31])=[N:13][CH:14]=1)(=[O:20])[NH2:19]

Participants

5

Reactant 2

HCID 21333249HCID 21333249, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21333201HCID 21333201, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 22.6 g of crude 1-{N-benzyl-N-[2-(5-carbamoyl-2-pyridyloxy)-ethyl]-amino}-3-(2-methyl-phenyloxy)-2-propanol in 230 ml of dioxane is hydrogenated in the presence of 2.3 g of a palladium-on-charcoal catalyst (5% strength) at 20°-30° C. and under atmospheric pressure, until an equimolar amount of hydrogen has been taken up. The catalyst is filtered off and the filtrate is evaporated under reduced pressure. The residue is recrystallised from ethyl methyl ketone and gives 1-[2-(5-carbamoyl-2-pyridyloxy)-ethylamino]-3-(2-methyl-phenyloxy)-2-propanol, melting point 139°-141° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated under reduced pressure
  3. customThe residue is recrystallised from ethyl methyl ketone

Sources & evidence

ORD record
ord-c922cb88017b4e42ad3c1d595eaf9a58
Source dataset
uspto-grants-1979_02
Patent number
US04139623

Reaction notes

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