(2-Azido-3-fluoro-propyl)benzene → 1-Fluoro-3-phenylpropan-2-amine

HRID 749299Notes

Reaction equation

HRID 749299 reaction equation
[N:1]([CH:4]([CH2:12][F:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[N+]=[N-]>CO.[Pd]>[F:13][CH2:12][CH:4]([NH2:1])[CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 22054864(2-Azido-3-fluoro-propyl)benzene

Product 1

HCID 50645991-Fluoro-3-phenylpropan-2-amineYield 74.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of (2-azido-3-fluoro-propyl)benzene (0.6 g) in MeOH (50 mL) was added 10% Pd/C catalyst and the suspension was hydrogenated for 2 hr. at 3 atmospheres pressure. The filtered reaction mixture and MeOH washings were concentrated to an oil which was chromatographed over silica gel with an ammoniated mixture of MeOH/ether (1:9) to give 0.38 g of the title compound. MS ES (M++H)=154.

Workup

  1. concentrationwere concentrated to an oil which
  2. customwas chromatographed over silica gel with an ammoniated mixture of MeOH/ether (1:9)

Sources & evidence

ORD record
ord-98fe17384f7148449a9ea79d8deada1b
Source dataset
uspto-grants-2008_07
Patent number
US07402604B2

Reaction notes

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