Propylamine → HCID 19778147, compound

HRID 2082333Notes

Reaction equation

HRID 2082333 reaction equation
Br[CH2:2]/[CH:3]=[CH:4]/[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH2:10]([NH2:13])[CH2:11][CH3:12].C(N(CC)CC)C>C(O)C>[CH2:10]([NH:13][CH2:2]/[CH:3]=[CH:4]/[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 7852PropylamineHCID 8471TriethylamineHCID 5373944Ethyl (E)-4-bromobut-2-enoate

Product 1

HCID 19778147HCID 19778147, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-bromocrotonate (21.4 g) was added dropwise to a solution of n-propylamine (11.8 g) and triethylamine (20.2 g) in ethanol (80 ml) at 0° C. under stirring and taking 1.5 hours, followed by stirring for 0.5 hours at room temperature. After removing the solvent, to the residue was added ethyl acetate, and the mixture was extracted with 1N hydrochloric acid. The extract was alkalified with potassium carbonate powder and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and distilled to remove the solvent to give 13.5 of the title compound as pale yellow oily substance.

Workup

  1. stirringby stirring for 0.5 hours at room temperature
  2. customAfter removing the solvent
  3. additionto the residue was added ethyl acetate
  4. extractionthe mixture was extracted with 1N hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationdistilled
  9. customto remove the solvent

Sources & evidence

ORD record
ord-56987a314cd641088d2692d5b9daed6e
Source dataset
uspto-grants-1993_02
Patent number
US05189043

Reaction notes

Loading…