Dipropylamine → HCID 86757982, compound

HRID 843655Notes

Reaction equation

HRID 843655 reaction equation
[CH2:1]([NH:4][CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].Br[CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([N:4]([CH:9]=[C:10]1[CH:11]=[CH:12][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:18][CH2:19]1)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 8902DipropylamineHCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 86757982HCID 86757982, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.37 cm3 of N,N-di-n-propylamine are added to a suspension of 2.29 g of methyl 4-(bromomethyl)benzoate and 1.52 g of potassium carbonate in 40 cm3 of acetonitrile, at a temperature close to 20° C. The reaction mixture is heated under reflux for about 16 hours, and then after cooling to a temperature close to 20° C., it is filtered on sintered glass. The sintered glass is rinsed with 3 times 30 cm3 of ethyl acetate. The filtrate is concentrated to dryness under reduced pressure at a temperature close to 40° C. After dissolution of the residue in 100 cm3 of ethyl acetate, the organic phase is successively washed with 3 times 100 cm3 of distilled water, 100 cm3 of a saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated to dryness under reduced pressure (about 1 kPa) at a temperature close to 40° C. 2.5 g of methyl 4-(N,N-di-n-propylaminomethylene)benzoate are thus obtained in the form of a yellow oil.

Workup

  1. customclose to 20° C
  2. temperatureThe reaction mixture is heated
  3. temperatureunder reflux for about 16 hours
  4. temperatureafter cooling to a temperature
  5. customclose to 20° C.
  6. filtrationit is filtered on sintered glass
  7. washThe sintered glass is rinsed with 3 times 30 cm3 of ethyl acetate
  8. concentrationThe filtrate is concentrated to dryness under reduced pressure at a temperature
  9. customclose to 40° C
  10. dissolutionAfter dissolution of the residue in 100 cm3 of ethyl acetate
  11. washthe organic phase is successively washed with 3 times 100 cm3 of distilled water, 100 cm3 of a saturated aqueous sodium chloride solution
  12. dry with materialdried over magnesium sulphate
  13. concentrationconcentrated to dryness under reduced pressure (about 1 kPa) at a temperature
  14. customclose to 40° C

Sources & evidence

ORD record
ord-ade5da23d245416791b65b50bedd9b8a
Source dataset
uspto-grants-2002_04
Patent number
US06380197B1

Reaction notes

Loading…