1-(1-(2-Fluoro-5-methoxy-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazine → 5-Fluoro-2-methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)aniline

HRID 1256023Notes

Reaction equation

HRID 1256023 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[N:13]1[CH2:18][CH2:17][CH:16]([N:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)[CH2:15][CH2:14]1>[Pd].CO>[F:1][C:2]1[C:3]([N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)[CH2:15][CH2:14]2)=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:7]=1)[NH2:8]

Participants

4

Reactant 1

HCID 580714331-(1-(2-Fluoro-5-methoxy-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazine

Product 1

HCID 580714395-Fluoro-2-methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)anilineYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-(1-(2-Fluoro-5-methoxy-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazine (1.65 g, 4.68 mmol) was added in a 200-mL round-bottomed flask. Methanol (30 mL) was added as the solvent. Pd/C (10% wet) (0.2 g, 4.68 mmol) was added. The reaction was stirred under a hydrogen balloon for 5 h. The filtrate was collected after filtration and it was concentrated in vacuo to give the title product (1.4 g, 93% yield).

Workup

  1. customThe filtrate was collected
  2. filtrationafter filtration and it
  3. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-538d318587e245ff9f5597478afdaf79
Source dataset
uspto-grants-2013_06
Patent number
US08461170B2

Reaction notes

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