1-(2-Fluoroethyl)-4-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine → 4-[4-[4-(2-Fluoroethyl)-1-piperazinyl]-1-piperidinyl]-2-(methyloxy)aniline

HRID 419365Notes

Reaction equation

HRID 419365 reaction equation
[F:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[C:18]([O:25][CH3:26])[CH:17]=3)[CH2:12][CH2:11]2)[CH2:6][CH2:5]1.[H][H]>CCOC(C)=O.[Pd]>[F:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([O:25][CH3:26])[CH:17]=3)[CH2:12][CH2:11]2)[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 598602761-(2-Fluoroethyl)-4-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazineHCID 178418361HCID 178418361, compound

Product 1

HCID 598602604-[4-[4-(2-Fluoroethyl)-1-piperazinyl]-1-piperidinyl]-2-(methyloxy)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

1-(2-fluoroethyl)-4-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine (27.13 g, 74.04 mmol) was taken up in EtOAc (1000 mL) and 10% Palladium on Carbon was added as a slurry in EtOAc. The reaction was placed under a balloon of hydrogen gas and was allowed to stir at rt for 3 days. The catalyst was filtered off and the filtrate was concentrated in vacuo to give the title compound of step F without further purification (24.25 g, 97%). MS (M+H, ES+) 337.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-120afd2a12e54cd8a08c59421d0cebfd
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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