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

HRID 258277Notes

Reaction equation

HRID 258277 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[O:10]1[CH2:25][CH:11]1[CH2:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19](=[O:24])[CH:18]=[CH:17]2>CO>[CH3:1][N:2]([CH2:25][CH:11]([OH:10])[CH2:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19](=[O:24])[CH:18]=[CH:17]2)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=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 72.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of N-methylbenzylamine (21 g) in methanol (50 ml), a solution of 6-(2,3-epoxypropoxy)carbostyril (4.4 g) in methanol (70 ml) is added dropwise over a period of 30 minutes under refluxing with heat. After the addition, the mixture is further heated with refluxing for 2 hours. The reaction mixture is concentrated 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 (5 g), as white powder, m.p. 129°-132° C.

Workup

  1. temperatureunder refluxing
  2. temperaturewith heat
  3. additionAfter the addition
  4. temperaturethe mixture is further heated
  5. temperaturewith refluxing for 2 hours
  6. concentrationThe reaction mixture is concentrated under reduced pressure
  7. customthe resulting residue is purified by silica gel column chromatography (solvent; methanol:chloroform=1:100-1:25)
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-b6fe6136f3904c6b92192de5639876f4
Source dataset
uspto-grants-1993_11
Patent number
US05266577

Reaction notes

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