Methyl iodide → 1-methyl-6-[3-(N-cyclohexyl-N-methylaminocarbonyl)propoxy]-3,4-dihydrocarbostyril

HRID 1154961Notes

Reaction equation

HRID 1154961 reaction equation
[CH:1]1([N:7]([CH3:25])[C:8]([CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19](=[O:24])[CH2:18][CH2:17]3)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[H][H].[CH3:30]I>CN(C=O)C>[CH3:30][N:20]1[C:21]2[C:16](=[CH:15][C:14]([O:13][CH2:12][CH2:11][CH2:10][C:8]([N:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH3:25])=[O:9])=[CH:23][CH:22]=2)[CH2:17][CH2:18][C:19]1=[O:24]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 13200334N-Cyclohexyl-N-methyl-4-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)butanamideHCID 178418361HCID 178418361, compound

Product 1

HCID 155729261-methyl-6-[3-(N-cyclohexyl-N-methylaminocarbonyl)propoxy]-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.7 g of 6-[3-(N-cyclohexyl-N-methylaminocarbonyl)propoxy]-3,4-dihydrocarbostyril in 50 ml of DMF is added 0.3 g of sodium hydroxide at room temperature under agitation. After the end of hydrogen generation, 1 ml of methyl iodide is added dropwise to the solution and the mixture is agitated at room temperature for 3 hours. After the reaction, the solvent is distilled off under reduced pressure and the residue is dissolved in 200 ml of chloroform. The chloroform layer is washed with an aqueous K2CO3 solution and water and then dried with anhydrous Na2SO4. After filtering out the inorganic matter, the mother liquor is concentrated and the residue is recrystallized from ligroin to obtain 0.9 g of 1-methyl-6-[3-(N-cyclohexyl-N-methylaminocarbonyl)propoxy]-3,4-dihydrocarbostyril in the form of colorless needle-like crystals with melting point of 104.5°-106.5° C.

Workup

  1. customAfter the reaction
  2. distillationthe solvent is distilled off under reduced pressure
  3. dissolutionthe residue is dissolved in 200 ml of chloroform
  4. washThe chloroform layer is washed with an aqueous K2CO3 solution and water
  5. dry with materialdried with anhydrous Na2SO4
  6. filtrationAfter filtering out the inorganic matter
  7. concentrationthe mother liquor is concentrated
  8. customthe residue is recrystallized from ligroin

Sources & evidence

ORD record
ord-de8daeb2e0d740a78b57ac25709dff4d
Source dataset
uspto-grants-1981_11
Patent number
US04298739

Reaction notes

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