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

HRID 1596771Notes

Reaction equation

HRID 1596771 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-592d83b7e45149a38976511aaefeca8a
Source dataset
uspto-grants-2001_09
Patent number
US06291683B1

Reaction notes

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