Dimethylamine → HCID 86149170, compound

HRID 373202Notes

Reaction equation

HRID 373202 reaction equation
Br.[N:2]1[CH:7]=CC=C[CH:3]=1.[C:8]([O:14][CH2:15][CH3:16])(=[O:13])[CH2:9][C:10]([CH3:12])=O.C[NH:18]C>C(Cl)Cl>[CH2:15]([O:14][C:8](=[O:13])[CH:9]=[C:10]([NH2:18])[CH2:12][N:2]([CH3:7])[CH3:3])[CH3:16]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8868Ethyl AcetoacetateHCID 87810Pyridine, hydrobromide (1:1)

Product 1

HCID 86149170HCID 86149170, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridine-hydrobromide-perbromide (48 g) was added to a solution of ethyl acetoacetate (19.4 g) in anhydrous methylene chloride (500 ml) at room temperature in 20 minutes. The mixture was stirred for 2 hours and then added dropwise to a solution of dimethylamine (48.8 g) in anhydrous methylene chloride (100 ml) at -15°-0° in 1 hr. The resulting mixture was cooled to -20° and ammonia was bubbled through the mixture under stirring for 1 hr and for 2 hr at room temperature. The reaction went to completion, by leaving the mixture overnight at about 5° C. After evaporation of the solvent the residue was treated with ether the solid was filtered off and the solution evaporated, to yield a brown oil, which was purified by column chromatography on silica gel to give the title compound (10.8 g) as an orange oil.

Workup

  1. temperatureThe resulting mixture was cooled to -20°
  2. customammonia was bubbled through the mixture
  3. stirringunder stirring for 1 hr and for 2 hr at room temperature
  4. customby leaving the mixture overnight at about 5° C
  5. customAfter evaporation of the solvent the residue
  6. additionwas treated with ether the solid
  7. filtrationwas filtered off
  8. customthe solution evaporated
  9. customto yield a brown oil, which
  10. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-af7e714da9d14b5386d0442c183c5a87
Source dataset
uspto-grants-1992_11
Patent number
US05162345

Reaction notes

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