HCID 15921594, compound → HCID 15572903, compound

HRID 1154944Notes

Reaction equation

HRID 1154944 reaction equation
[N+](C1C=CC(O[C:9]([CH2:11][CH:12]([CH3:26])[CH2:13][O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[NH:21][C:20](=[O:25])[CH:19]=[CH:18]3)=[O:10])=CC=1)([O-])=O.[CH3:29][NH:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]1[CH3:37]>CN(C)C=O>[CH3:29][N:30]([CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]1[CH3:37])[C:9]([CH2:11][CH:12]([CH3:26])[CH2:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20](=[O:25])[CH:19]=[CH:18]2)=[O:10]

Participants

4

Reactant 2

HCID 15921594HCID 15921594, compoundHCID 20563606HCID 20563606, compound

Product 1

HCID 15572903HCID 15572903, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.8 Grams of 6-[3-(p-nitrophenoxycarbonyl)-2-methylpropoxy]carbostyril is dissolved in 40 ml of dimethylformamide, followed by addition of 1.6 ml of N-methyl-2-methylcyclohexylamine and 12-hour agitation at 60°-70° C. After the reaction, the solvent is distilled off and the obtained residue is refined by silica gel column chromatography (silica gel: Wakogel C-200; eluent: 20/1 (V/V) chloroform/methanol) and the crude crystals are recrystallized from benzene-ligroin to obtain 1.6 g of 6-{3-[N-methyl-N-(2-methylcyclohexyl)aminocarbonyl]-2-methylpropoxy}carbostyril in the form of colorless needlelike crystals with melting point of 146°-149° C.

Workup

  1. customAfter the reaction
  2. distillationthe solvent is distilled off
  3. customthe crude crystals are recrystallized from benzene-ligroin

Sources & evidence

ORD record
ord-554fb7ef4a1a412e9fa21916426d62c3
Source dataset
uspto-grants-1981_11
Patent number
US04298739

Reaction notes

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