HCID 21333283, compound → HCID 21333254, compound

HRID 2399153Notes

Reaction equation

HRID 2399153 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[C:17]([C:18](=[O:20])[NH2:19])=[CH:16][CH:15]=[CH:14][N:13]=1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[C:18]([C:17]1[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]=[CH:15][CH:16]=1)(=[O:20])[NH2:19]

Participants

5

Reactant 2

HCID 21333283HCID 21333283, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21333254HCID 21333254, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 11.7 g of 1-{N-benzyl-N-[2-(3-carbamoyl-2-pyridyloxy)-ethyl]-amino}-3-(2-methyl-phenyloxy)-2-propanol in 120 ml of ethanol is hydrogenated in the presence of 1.2 g of a 5% strength palladium-on-charcoal catalyst at 20°-30° C. and under atmospheric pressure until the uptake of hydrogen ceases. The reaction product is worked up analogously to the process described in Example 1, giving crude 1-[2-(3-carbamoyl-2-pyridyloxy)-ethylamino]-3-(2-methyl-phenyloxy)-2-propanol. A solution of 1.5 g of fumaric acid in isopropanol is added thereto and the neutral fumaric acid salt of 1-[2-(3-carbamoyl-2-pyridyloxy)-ethyl-amino]-3-(2-methyl-phenyloxy)-2-propanol thus obtainable, is recrystallised from a mixture of isopropanol and water; melting point 156° C.

Sources & evidence

ORD record
ord-04b560eeb509449bb67988bcd442e9fa
Source dataset
uspto-grants-1977_05
Patent number
US04027027

Reaction notes

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