4-Fluoro-2-nitro-5-(2-piperidin-1-ylethoxy)-phenylamine → 4-Fluoro-5-(2-piperidin-1-ylethoxy)benzene-1,2-diamine

HRID 2274387Notes

Reaction equation

HRID 2274387 reaction equation
[F:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:6][C:5]([NH2:17])=[C:4]([N+:18]([O-])=O)[CH:3]=1.[H][H]>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([NH2:18])[C:5]([NH2:17])=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 688421034-Fluoro-2-nitro-5-(2-piperidin-1-ylethoxy)-phenylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 688419974-Fluoro-5-(2-piperidin-1-ylethoxy)benzene-1,2-diamineYield 95.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

443 mg of 4-fluoro-2-nitro-5-(2-piperidin-1-ylethoxy)-phenylamine in solution in 20 mL of methanol are hydrogenated under 1 bar of hydrogen pressure in the presence of 44 mg of palladium-on-charcoal at 25° C. for 10 hours. The reaction crude is filtered through celite and the filtrate is concentrated under vacuum in a rotary evaporator. 380 mg of 4-fluoro-5-(2-piperidin-1-ylethoxy)benzene-1,2-diamine are obtained in the form of a black lake. The compound is used without any other purification.

Workup

  1. customThe reaction crude
  2. filtrationis filtered through celite
  3. concentrationthe filtrate is concentrated under vacuum in a rotary evaporator

Sources & evidence

ORD record
ord-f960b1c2438d4fea81fa247729c7257c
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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