Potassium Carbonate → 1-methyl-6-[3-(N-cyclohexyl-N-methylaminocarbonyl)-propoxy]carbostyril

HRID 1154954Notes

Reaction equation

HRID 1154954 reaction equation
[CH3:1][N:2]1[C:12]2[C:7](=[CH:8][C:9]([OH:13])=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:3]1=[O:4].C([O-])([O-])=O.[K+].[K+].[CH3:20][N:21]([CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[C:22](=[O:27])[CH2:23][CH2:24][CH2:25]Cl>CN(C=O)C>[CH3:1][N:2]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH2:25][CH2:24][CH2:23][C:22]([N:21]([CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]3)[CH3:20])=[O:27])=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:3]1=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 128032046-Hydroxy-1-methylquinolin-2(1H)-oneHCID 132082974-Chloro-N-cyclohexyl-N-methylbutanamide

Product 1

HCID 155729251-methyl-6-[3-(N-cyclohexyl-N-methylaminocarbonyl)-propoxy]carbostyril

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.75 Grams of 1-methyl-6-hydroxycarbostyril, 1.8 g of K2CO3 and 0.5 g of KI are added to 50 ml of DMF, and then 2.8 g of N-methyl-N(4-chlorobutyryl)cyclohexylamine is added gradually dropwise to this solution at 60° to 70° C. under agitation, followed by additional 4-hour agitation at the same temperature and removal of the solvent by distillation. The residue is dissolved in 200 ml of chloroform, washed with diluted hydrochloric acid, a 1% aqueous NaOH solution and water and then dried with anhydrous Na2SO4. After filtering off the inorganic matter, the mother liquor is concentrated and the residue is crystallized from petroleum ether. The obtained crystals are recrystallized from benzene-ligroin to produce 0.6 g of 1-methyl-6-[3-(N-cyclohexyl-N-methylaminocarbonyl)-propoxy]carbostyril in the form of colorless needle-like crystals with melting point of 118.5°-119.5° C.

Workup

  1. waitfollowed by additional 4-hour
  2. customagitation at the same temperature and removal of the solvent
  3. distillationby distillation
  4. dissolutionThe residue is dissolved in 200 ml of chloroform
  5. washwashed with diluted hydrochloric acid
  6. dry with materiala 1% aqueous NaOH solution and water and then dried with anhydrous Na2SO4
  7. filtrationAfter filtering off the inorganic matter
  8. concentrationthe mother liquor is concentrated
  9. customthe residue is crystallized from petroleum ether
  10. customThe obtained crystals are recrystallized from benzene-ligroin

Sources & evidence

ORD record
ord-ffa54ae19435442c83bbd618cb062d4e
Source dataset
uspto-grants-1981_11
Patent number
US04298739

Reaction notes

Loading…