N-Methylbenzylamine → 6-[3-(N-methyl-N-benzylamino)-2-hydroxypropoxy]carbostyril

HRID 258275Notes

Reaction equation

HRID 258275 reaction equation
Cl[CH2:2][CH:3]([OH:17])[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH:10]=[CH:9]2.[CH3:18][NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[CH3:18][N:19]([CH2:2][CH:3]([OH:17])[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH:10]=[CH:9]2)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 7669N-MethylbenzylamineHCID 200954426-(3-Chloro-2-hydroxypropoxy)carbostyril

Product 1

HCID 103597756-[3-(N-methyl-N-benzylamino)-2-hydroxypropoxy]carbostyrilYield 37.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-(3-chloro-2-hydroxypropoxy)-carbostyril (5.05 g) and N-methylbenzylamine (6.0 g) in dimethylformamide (50 ml) is heated with stirring at 50°-60° C. for 5 hours. The solvent is distilled off under reduced pressure and the resulting residue is purified by silica gel column chromatography (solvent; methanol:chloroform=1:100-1:25) and recrystallized from ethanol to give 6-[3-(N-methyl-N-benzylamino)-2-hydroxypropoxy]carbostyril (2.5 g), as white powder, m.p. 129°-132° C.

Workup

  1. distillationThe solvent is distilled off under reduced pressure
  2. customthe resulting residue is purified by silica gel column chromatography (solvent; methanol:chloroform=1:100-1:25)
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-caf7430908df44fd8c3781c057e9f447
Source dataset
uspto-grants-1993_11
Patent number
US05266577

Reaction notes

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