Diethylamine → HCID 58615365, compound

HRID 852995Notes

Reaction equation

HRID 852995 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2Cl.[CH2:13]([NH:15][CH2:16][CH3:17])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[N:15]([CH2:16][CH3:17])[CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 8021Diethylamine2×HCID 11430Potassium CarbonateHCID 51395376-Bromo-4-chloroquinoline2×

Product 1

HCID 58615365HCID 58615365, compoundYield 17.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 6-bromo-4-chloro-quinoline (0.900 g, 3.71 mmol) and diethylamine (1.364 g, 18.56 mmol) in ethanol (10 mL) was added potassium carbonate (2.56 g, 18.56 mmol) at room temperature. Then, the reaction mixture was stirred for 15 h in a sealed tube. TLC analysis of the reaction mixture indicated the presence of lot of 6-bromo-4-chloro-quinoline and another 2 mL of diethylamine was added and heated to 100° C. and stirred for 15 h. After cooling to room temperature, the reaction mixture was diluted with water and the solvent was removed under the vacuum. Then, the product was extracted with ethyl acetate (3×50 mL). The combined extracts were washed with brine solution and dried over anhydrous magnesium sulfate. After filtration of the drying agent, the filtrate was removed under the vacuum and the residue was purified by using a Biotage silica gel column chromatography to afford 0.180 g (17.4% yield) of (6-bromo-quinolin-4-yl)-diethylamine as a light yellow oil: EI-LRMS m/e calcd for C13H15BrN2 (M+) 279.1, found 279.1.

Workup

  1. stirringstirred for 15 h
  2. temperatureAfter cooling to room temperature
  3. customthe solvent was removed under the vacuum
  4. extractionThen, the product was extracted with ethyl acetate (3×50 mL)
  5. washThe combined extracts were washed with brine solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtration of the drying agent
  8. customthe filtrate was removed under the vacuum
  9. customthe residue was purified

Sources & evidence

ORD record
ord-93a62d1e1f1248519875d2f32a5593eb
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

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