5-Fluoro-indolyl-3-propylazide → 5-Fluoro-indolyl-3-propylamine

HRID 1954222Notes

Reaction equation

HRID 1954222 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](C(N=[N+]=[N-])CC)=[CH:5]2>[Pd].C(O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([NH:7][CH2:6][CH2:5][CH3:4])=[CH:5]2

Participants

4

Reactant 1

HCID 543589695-Fluoro-indolyl-3-propylazide

Product 1

HCID 699484305-Fluoro-indolyl-3-propylamineYield 121.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-fluoro-indolyl-3-propylazide (8 g, 0.037 mol) and 10% palladium on carbon in ethanol was hydrogenated at 50 psi for 16 hours. The catalyst was filtered and the solvent removed under vacuum. The celite was washed with methanol (300 ml) and the solvent was removed under vacuum. Chromatography (15% methanol-methylene chloride plus ammonium hydroxide) afforded 4.33 g (61%) of product as a yellow solid: mp 82-84.5° C.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent removed under vacuum
  3. washThe celite was washed with methanol (300 ml)
  4. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-81c9fd9dac2a4cb9b8e3e7d862316920
Source dataset
uspto-grants-2000_09
Patent number
US06121307

Reaction notes

Loading…