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

HRID 1770133Notes

Reaction equation

HRID 1770133 reaction equation
[O:1]1[CH2:16][CH:2]1[CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH:9]=[CH:8]2.[CH3:17][NH:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CO>[CH3:17][N:18]([CH2:16][CH:2]([OH:1])[CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH:9]=[CH:8]2)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 7669N-MethylbenzylamineHCID 150155236-(Oxiran-2-ylmethoxy)quinolin-2(1H)-one

Product 1

HCID 103597756-[3-(N-methyl-N-benzylamino)-2-hydroxypropoxy]carbostyrilYield 32.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 6-(2,3-epoxypropoxy)carbostyril (15 g) and N-methylbenzylamine (11 g) in methanol (150 ml) is heated with refluxing for 2.5 hours. From the mixture, methanol is distilled off under reduced pressure, and to the resulting residue is added diethylether and the precipitated crystals are collected by filtration. The crystals thus obtained are 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 (7.6 g), as white powder, m.p. 129°-132° C.

Workup

  1. temperatureis heated
  2. temperaturewith refluxing for 2.5 hours
  3. distillationFrom the mixture, methanol is distilled off under reduced pressure
  4. additionto the resulting residue is added diethylether
  5. filtrationthe precipitated crystals are collected by filtration
  6. customThe crystals thus obtained
  7. customare purified by silica gel column chromatography (solvent; methanol:chloroform=1:100-1:25)
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-5262647548a14c26ac869caa309d5ce2
Source dataset
uspto-grants-1995_01
Patent number
US05385914

Reaction notes

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