Sodium Hydroxide → 3-[2-(N,N-Dimethylamino)ethyl]-1,2,3,4-tetrahydroquinoline

HRID 2269714Notes

Reaction equation

HRID 2269714 reaction equation
[CH3:1][N:2]([CH3:17])[C:3](=O)[CH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]1=O.[OH-].[Na+]>Cl>[CH3:1][N:2]([CH2:3][CH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH2:6]1)[CH3:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10585665N,N-Dimethyl-2-oxo-1,2,3,4-tetrahydro-3-quinolineacetoamide

Product 1

HCID 183331263-[2-(N,N-Dimethylamino)ethyl]-1,2,3,4-tetrahydroquinolineYield 75.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Borane-THF complex (1M; 15 ml) was added to N,N-dimethyl-2-oxo-1,2,3,4-tetrahydro-3-quinolineacetoamide (590 mg), which was heated under reflux for 3.5 hours. 6N hydrochloric acid (10 ml) was added to the reaction mixture, which was heated under reflux overnight. 6N sodium hydroxide was added to the reaction mixture to adjust pH to 7 and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, then dried and concentrated. The residue was purified by alumina column chromatography (eluent: hexane/ethyl acetate=1/1) to obtain the entitled compound (390 mg) as an oily substance.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3.5 hours
  3. temperaturewas heated
  4. temperatureunder reflux overnight
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution
  7. dry with materiala saturated aqueous sodium chloride solution, then dried
  8. concentrationconcentrated
  9. customThe residue was purified by alumina column chromatography (eluent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-5e6b2901d14c47e4aba22c49b92f3992
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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