Hydrochloric Acid → 289050-73-3

HRID 1793789Notes

Reaction equation

HRID 1793789 reaction equation
[N:1]([CH2:4][CH:5]([OH:18])[CH2:6][N:7]1[C:11](=[O:12])[C:10]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]2[C:8]1=[O:17])=[N+]=[N-].[ClH:19].[H][H]>[Pd].C(O)C>[ClH:19].[NH2:1][CH2:4][CH:5]([OH:18])[CH2:6][N:7]1[C:11](=[O:12])[C:10]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]2[C:8]1=[O:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10857754N-(3-Azido-2-hydroxypropyl)phthalimideHCID 178418361HCID 178418361, compound

Product 1

HCID 22219128289050-73-3

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To ethanol solution (240 ml) of N-(3-azido-2-hydroxypropyl)phthalimide 10 g (40.3 mol), 10% Pd—C (1 g) and concentrated hydrochloric acid solution 7.84 ml (80.6 mmol) were added sequentially. To the reaction mixture, hydrogen was introduced at 2 kgf/cm2 atm. and hydrogenated at room temperature for 6 hours. After removal of catalyst by filtration, catalyst was washed with EtOH/DMF (1:1) solution (300 ml) and then combined filtrate was evaporated to dryness. Addition of EtOH to the residue gave crystal of desired product as hydrogen chloride salt. Crystal was collected by filtration and dried under reduced pressure at 40° C. to afford 5.3 g of the product. The NMR spectra were consistent with the desired title intermediate.

Workup

  1. customAfter removal of catalyst
  2. filtrationby filtration, catalyst
  3. washwas washed with EtOH/DMF (1:1) solution (300 ml)
  4. customcombined filtrate was evaporated to dryness
  5. additionAddition of EtOH to the residue

Sources & evidence

ORD record
ord-5014fafc69d046df8906319f48d0ad7c
Source dataset
uspto-grants-2006_04
Patent number
US07022677B1

Reaction notes

Loading…