Diethylcarbamoyl chloride → HCID 13077557, compound

HRID 542850

Reaction equation

HRID 542850 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH3:26].C(=O)([O-])[O-].[Na+].[Na+].[CH2:33]([N:35]([CH2:39][CH3:40])[C:36]([Cl:38])=[O:37])[CH3:34]>CC(C)=O>[ClH:38].[ClH:38].[CH2:33]([N:35]([CH2:39][CH3:40])[C:36]([N:23]1[CH2:22][CH2:21][N:20]([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:13][C:11]2[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]3[C:10]=2[N:9]=[CH:8][CH:7]=[C:6]3[CH3:26])[CH2:25][CH2:24]1)=[O:37])[CH3:34]

Participants

5

Reactant 3

HCID 6916Diethylcarbamoyl chlorideHCID 10340Sodium CarbonateHCID 130775336-Methoxy-4-methyl-N-[6-(1-piperazinyl)hexyl]-8-quinolinamine

Product 1

HCID 13077557HCID 13077557, compoundYield 108.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a mixture of 2.4 g (0.00673 mole) of 6-methoxy-4-methyl-N-[6-(1-piperazinyl)hexyl]-8-quinolinamine and 1.7 g (0.016 mole) of sodium carbonate in 50 ml of acetone was added a solution of 1.8 g (0.007 mole) of diethylcarbamoylchloride in 20 ml of acetone. The mixture was stirred under gentle reflux for 2 hr, allowed to cool, filtered and concentrated to dryness in vacuo. A solution of the residue in dichloromethane was washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated to dryness. Chromatography of the residue over 70 g of silica with 10% methanol in ethyl acetate afforded 2 g of product, Rf=0.3. The material was triturated with 2-propanol containing excess hydrogen chloride. The resulting yellow precipitate was collected, washed with 2-propanol and then ether, dried in vacuo at 52° overnight and air-equilibrated to afford 1.8 g (50%) of the title compound, mp 226°-228° (dec).

Workup

  1. temperatureunder gentle reflux for 2 hr
  2. temperatureto cool
  3. filtrationfiltered
  4. concentrationconcentrated to dryness in vacuo
  5. washA solution of the residue in dichloromethane was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-74aafbe616004e3aa64c099d8cfe2ff9
Source dataset
uspto-grants-1987_04
Patent number
US04659708

Linked notes

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