HCID 10319158, compound → HCID 53931874, compound

HRID 1462354Notes

Reaction equation

HRID 1462354 reaction equation
[C:1]([C:4]1[CH:29]=[CH:28][C:7]([O:8][CH2:9][CH2:10][N:11](CC2C=CC=CC=2)[CH2:12][CH:13]([OH:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][C:5]=1[OH:30])(=[O:3])[NH2:2]>CO.[Pd]>[C:1]([C:4]1[CH:29]=[CH:28][C:7]([O:8][CH2:9][CH2:10][NH:11][CH2:12][CH:13]([OH:20])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:6][C:5]=1[OH:30])(=[O:3])[NH2:2]

Participants

4

Reactant 1

HCID 10319158HCID 10319158, compound

Product 1

HCID 53931874HCID 53931874, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 15 g of crude N-[2-(4-carbamoyl-3-hydroxyphenoxy)-ethyl]-N-(2-hydroxy-2-phenyl-ethyl)-benzylamine in 150 ml of methanol is hydrogenated under normal conditions, with the addition of 3 g of palladium-on-charcoal catalyst (5%), until the reaction has ceased. The catalyst is filtered off, the solvent is evaporated off and the residue is recrystallised from isopropanol. α-[N-[2-(4-Carbamoyl-3-hydroxy-phenoxy)-ethyl]-aminomethyl]-benzyl alcohol with a melting point of 141°-142° is obtained. The compound forms a hydrochloride with a melting point of 240°-242°.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solvent is evaporated off
  3. customthe residue is recrystallised from isopropanol

Sources & evidence

ORD record
ord-e29cd9d7d7154916af502e136cd003e5
Source dataset
uspto-grants-1984_07
Patent number
US04460580

Reaction notes

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