2-Aminoquinoline → HCID 21939951, compound

HRID 1242873Notes

Reaction equation

HRID 1242873 reaction equation
[N:1]1([CH2:7][CH2:8][CH:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH2:20][C:21]4[CH:29]=[CH:28][C:24]([C:25]([O-])=[O:26])=[CH:23][CH:22]=4)[CH:15]=3)[CH2:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(C)(C)C(Cl)=O.[NH2:37][C:38]1[CH:47]=[CH:46][C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[N:39]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.C1COCC1.C(N(CC)CC)C>[N:1]1([CH2:7][CH2:8][CH:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH2:20][C:21]4[CH:22]=[CH:23][C:24]([C:25]([NH:37][C:38]5[CH:47]=[CH:46][C:45]6[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=6)[N:39]=5)=[O:26])=[CH:28][CH:29]=4)[CH:15]=3)[CH2:10]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

8

Reactant 4

HCID 113792-AminoquinolineHCID 62493Pivaloyl chlorideHCID 516892Sodium BicarbonateHCID 21939875HCID 21939875, compound

Product 1

HCID 21939951HCID 21939951, compoundYield 11.3%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (0.22 ml) was added to THF suspension (6 ml) of 4-[[2-(2-piperidinoethyl)-6-tetralinyl]oxymethyl]benzoate (300 mg). Further, trimethylacetyl chloride (0.095 ml) was added dropwise to under ice-cooling, which was stirred for 30 minutes. The temperature of the reaction mixture was raised to room temperature, which was stirred for 1 hour. THF solution (1.0 ml) of 2-aminoquinoline (170 mg) was added dropwise to the reaction mixture under ice-cooling, which was stirred at room temperature for 12 hours. Saturated sodium bicarbonate solution was added to the reaction mixture, and extraction was conducted using ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride solution, dried, and then concentrated. The residue was purified using alumina column chromatography (development solvent: THF), and recrystallized (ethyl acetate-diisopropyl ether) to give the titled compound (45 mg).

Workup

  1. temperaturecooling
  2. stirringwhich was stirred for 1 hour
  3. temperaturecooling
  4. stirringwhich was stirred at room temperature for 12 hours
  5. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified
  9. customrecrystallized (ethyl acetate-diisopropyl ether)

Sources & evidence

ORD record
ord-bcc7fbc9125548af9e64f1d039480aee
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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