2-Chloro-N,N-dimethylethylamine → HCID 18919267, compound

HRID 1291406Notes

Reaction equation

HRID 1291406 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:13])[N:4]=[C:3]1[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:30])[C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[CH:18][CH:17]=1.[CH3:31][N:32]([CH3:36])[CH2:33][CH2:34][Cl:35].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[ClH:35].[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:13])[N:4]=[C:3]1[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:30])[C:23]2[CH:24]=[CH:25][C:26]([O:29][CH2:34][CH2:33][N:32]([CH3:36])[CH3:31])=[CH:27][CH:28]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 11430Potassium CarbonateHCID 18919039HCID 18919039, compound

Product 1

HCID 18919267HCID 18919267, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3,5-dimethyl-2-[2-[4-(4-hydroxy-benzoyl)phenyl]ethyl]-4(3H)-quinazolinone (534 mg) in DMF (10 ml) were added 2-dimethylaminoethyl chloride (695 mg) and potassium carbonate (677 mg) and the mixture was stirred at 80° C. for 4 hours. This reaction mixture was concentrated and extracted with ethyl acetate. The organic layer was serially washed with water and saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, and concentrated to 20 ml. To this organic solution was added 1N-hydrochloric acid (2 ml) and the mixture was extracted with water. The aqueous layer was diluted with saturated aqueous NaHCO3 solution and extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl solution and dried over anhydrous magnesium sulfate. After concentration to 10 ml, 4N-hydrogen chloride/ethyl acetate (0.5 ml) was added, and the precipitate was collected by filtration, washed with water, and dried to provide 240 mg of white powder.

Workup

  1. concentrationThis reaction mixture was concentrated
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was serially washed with water and saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated to 20 ml
  6. additionTo this organic solution was added 1N-hydrochloric acid (2 ml)
  7. extractionthe mixture was extracted with water
  8. additionThe aqueous layer was diluted with saturated aqueous NaHCO3 solution
  9. extractionextracted with ethyl acetate
  10. washThe organic layer was washed with saturated aqueous NaCl solution
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationAfter concentration to 10 ml, 4N-hydrogen chloride/ethyl acetate (0.5 ml)
  13. additionwas added
  14. filtrationthe precipitate was collected by filtration
  15. washwashed with water
  16. customdried

Sources & evidence

ORD record
ord-c6c84d1f74b24d149c9f21f65de73367
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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