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

HRID 1154955Notes

Reaction equation

HRID 1154955 reaction equation
[CH3:1][N:2]1[C:12]2[C:7](=[CH:8][C:9]([OH:13])=[CH:10][CH:11]=2)[CH2:6][CH2:5][C:3]1=[O:4].[OH-].[K+].[I-].[Na+].[CH3:18][N:19]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C:20](=[O:25])[CH2:21][CH2:22][CH2:23]Cl.[Na+].[Cl-]>CS(C)=O>[CH3:1][N:2]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH2:23][CH2:22][CH2:21][C:20]([N:19]([CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]3)[CH3:18])=[O:25])=[CH:10][CH:11]=2)[CH2:6][CH2:5][C:3]1=[O:4]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 5238Sodium IodideHCID 14797Potassium HydroxideHCID 132082974-Chloro-N-cyclohexyl-N-methylbutanamideHCID 219318286-Hydroxy-1-methyl-3,4-dihydroquinolin-2(1H)-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3.4 Grams of 1-methyl-6-hydroxy-3,4-dihydrocarbostyril, 0.9 g of potassium hydroxide, 3.2 g of sodium iodide and 5.0 g of N-methyl-N-(4-chlorobutyryl)-cyclohexylamine are added to 50 ml of dimethylsulfoxide and agitated at 70° to 80° C. for 4.5 hours. After the reaction, the reaction solution is poured into 400 ml of saturated NaCl solution and the precipitated crystals are filtered out and washed with water. The resultant crude crystals are recrystallized from ligroin to obtain 3.1 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. filtrationthe precipitated crystals are filtered out
  3. washwashed with water
  4. customThe resultant crude crystals are recrystallized from ligroin

Sources & evidence

ORD record
ord-aa3ec323e8884819b08c252bec27136e
Source dataset
uspto-grants-1981_11
Patent number
US04298739

Reaction notes

Loading…