HCID 58032133, compound → 4-[4-(3,4-Difluorophenyl)-1-piperidinyl]-3,5-difluorobenzenamine

HRID 1429239Notes

Reaction equation

HRID 1429239 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([F:11])[C:3]=1[N:12]1[CH2:17][CH:16]=[C:15]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([F:25])[CH:19]=2)[CH2:14][CH2:13]1>C1COCC1.[Pd]>[F:25][C:20]1[CH:19]=[C:18]([CH:15]2[CH2:14][CH2:13][N:12]([C:3]3[C:4]([F:11])=[CH:5][C:6]([NH2:8])=[CH:7][C:2]=3[F:1])[CH2:17][CH2:16]2)[CH:23]=[CH:22][C:21]=1[F:24]

Participants

4

Reactant 1

HCID 58032133HCID 58032133, compound

Product 1

HCID 580320614-[4-(3,4-Difluorophenyl)-1-piperidinyl]-3,5-difluorobenzenamineYield 100.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2,6-difluoro-4-nitrophenyl)-4-(3,4-difluorophenyl)-1,2,3,6-tetrahydropyridine (0.67 g, 1.90 mmol) in THF (20 mL) was added 10% Pd on carbon (50 mg). The reaction flask was flushed with N2 gas, and the resulting mixture was vigorously stirred under 1 atm H2 gas for 24 hours. The mixture was filtered through diatomaceous earth and concentrated in vacuo to give the title compound as a solid (0.62 g, 100%).

Workup

  1. customThe reaction flask was flushed with N2 gas
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26ccc074a8774b678cd34c634009ce63
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

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