Methylamine → 6-(3-Methylaminopropoxy)carbostyril

HRID 1856755Notes

Reaction equation

HRID 1856755 reaction equation
Cl[CH2:2][CH2:3][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.[CH3:17][NH2:18]>CO>[CH3:17][NH:18][CH2:2][CH2:3][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

Participants

4

Reactant 2

HCID 6329MethylamineHCID 142894806-(3-Chloropropoxy)carbostyril

Product 1

HCID 130557376-(3-Methylaminopropoxy)carbostyril

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

6-(3-Chloropropoxy)carbostyril (20 g) is added into a 40% solution of methylamine in methanol (200 ml), and the mixture is heated with stirring at 100° C. overnight in a sealed tube. The mixture is concentrated under reduced pressure to remove the solvent, and the precipitated crystals are washed with a mixture of chloroform-diethyl ether, purified by silica gel column chromatography (solvent; methylene chloride:methanol:aqueous ammonia=50:10:1), and recrystallized from chloroform-diethyl ether to give 6-(3-methylaminopropoxy)carbostyril (15.4 g).

Workup

  1. temperaturethe mixture is heated
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customto remove the solvent
  4. washthe precipitated crystals are washed with a mixture of chloroform-diethyl ether
  5. custompurified by silica gel column chromatography (solvent; methylene chloride:methanol:aqueous ammonia=50:10:1)
  6. customrecrystallized from chloroform-diethyl ether

Sources & evidence

ORD record
ord-7c59b79eb9ce49af827f67f5b2a807a4
Source dataset
uspto-grants-2000_11
Patent number
US06143763

Reaction notes

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