Sodium Iodide → HCID 22329113, compound

HRID 586920Notes

Reaction equation

HRID 586920 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[I-].[Na+].[CH:14]1([NH2:17])[CH2:16][CH2:15]1>>[CH:14]1([NH:17][CH2:2][CH2:3][CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH2:16][CH2:15]1

Participants

4

Reactant 3

HCID 5238Sodium IodideHCID 69828CyclopropylamineHCID 2757253tert-Butyl 4-bromobutanoate

Product 1

HCID 22329113HCID 22329113, compound

Procedure

To cyclopropylamine (50 ml) was added dropwise t-butyl 4-bromobutyrate (33.5 g) at 40° C. To the mixture was added sodium iodide (22.6 g), and the mixture was refluxed overnight. The solvent was evaporated, and to the residue was added water. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine and dried with anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by distillation under reduced pressure to give t-butyl N-cyclopropyl-4-aminobutyrate (12.6 g) as colorless oil.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customThe solvent was evaporated
  3. additionto the residue was added water
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with water and saturated brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. distillationthe residue was purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-5864445c7f4d453e96a46aa9ab285935
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

Loading…