N-methyl-2-pyrrolidone → HCID 21183904, compound

HRID 1384920Notes

Reaction equation

HRID 1384920 reaction equation
Cl[C:2]1[CH:11]=[C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:23])[CH:8]=2)[N:3]=1.[NH:24]1[CH2:34][CH2:33][CH:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:26][CH2:25]1.CN1CCCC1=O>O>[CH2:31]([O:30][C:28]([CH:27]1[CH2:33][CH2:34][N:24]([C:2]2[CH:11]=[C:10]([NH:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]4[O:20][CH2:21][O:22][C:16]=4[CH:15]=3)[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([Cl:23])[CH:8]=3)[N:3]=2)[CH2:25][CH2:26]1)=[O:29])[CH3:32]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 70770Ethyl 4-piperidinecarboxylateHCID 21183988HCID 21183988, compound

Product 1

HCID 21183904HCID 21183904, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction of a mixture comprising 130 mg of 2,6-dichloro-4-(3,4-methylenedioxybenzyl)aminoquinoline, 500 μl of ethyl isonipecotate and 1 ml of N-methyl-2-pyrrolidone was conducted on an oil bath at 150° C. for 3 hours. The reaction mixture was cooled, followed by the addition of water. The resulting mixture was extracted with ethyl acetate and the ethyl acetate layer was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography with 20 to 50% ethyl acetate/hexane to give 150 mg of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washthe ethyl acetate layer was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography with 20 to 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-a84d989318d947c0877eae7ba54d2c4b
Source dataset
uspto-grants-2001_07
Patent number
US06262059B1

Reaction notes

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