1-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)-2-(ethyl(methyl)amino)ethanone → 2-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)-N-ethyl-N-methylethanamine

HRID 1922459Notes

Reaction equation

HRID 1922459 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=O)[CH2:13][N:14]([CH2:16][CH3:17])[CH3:15])[CH2:7][CH2:6][CH2:5]2>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][N:14]([CH2:16][CH3:17])[CH3:15])[CH2:7][CH2:6][CH2:5]2

Participants

4

Reactant 1

HCID 573435551-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)-2-(ethyl(methyl)amino)ethanone

Product 1

HCID 573435582-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)-N-ethyl-N-methylethanamineYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)-2-(ethyl(methyl)amino)ethanone (1.05 g, 3.37 mmol) in THF (10 mL) was cooled to 0° C. then treated with BH3 in THF (1M) (33.7 mL, 33.7 mmol). The clear solution was allowed to warm to room temperature and stirred at this temperature for 3 days. The mixture was cooled to 0° C. and treated with methanol (5 mL) dropwise with caution. After stirring for 15 minutes, the mixture was concentrated to dryness then dissolved in methanol (25 mL) and concentrated again. The residue was dissolved in 25 mL methanol and heated at reflux for 5 hours then stirred at room temperature overnight. The reaction was concentrated to dryness to give a light yellow residue. This residue was subjected to flash chromatography on silica gel using 5% 2M NH3 in MeOH/95% CH2Cl2 to give a colourless residue (0.89 g, 89%). 1H-NMR (CDCl3) δ 7.09 (dd, J=1.8, 6.6 Hz, 1H), 7.02-7.01 (m, 1H), 6.44 (d, J=6.6 Hz, 1H), 3.36 (t, J=5.7 Hz, 2H), 3.29 (t, J=4.2 Hz, 2H), 2.70 (t, J=4.8 Hz, 2H), 2.53-2.43 (m, 4H), 2.28 (s, 3H), 1.94-1.88 (m, 2H), 1.06 (t, J=5.4 Hz, 3H). MS (ESI): 397.1 and 399.1 (M+1, 100%).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringAfter stirring for 15 minutes
  3. concentrationthe mixture was concentrated to dryness
  4. dissolutionthen dissolved in methanol (25 mL)
  5. concentrationconcentrated again
  6. dissolutionThe residue was dissolved in 25 mL methanol
  7. temperatureheated
  8. temperatureat reflux for 5 hours
  9. stirringthen stirred at room temperature overnight
  10. concentrationThe reaction was concentrated to dryness
  11. customto give a light yellow residue

Sources & evidence

ORD record
ord-fd7ebd139e0048e6a9529f1cf69b299d
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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