4-Fluoro-2-nitro-5-(3-piperidin-1-ylpropoxy)phenylamine → 4-Fluoro-5-(3-piperidin-1-ylpropoxy)benzene-1,2-diamine

HRID 2274395Notes

Reaction equation

HRID 2274395 reaction equation
[F:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:6][C:5]([NH2:18])=[C:4]([N+:19]([O-])=O)[CH:3]=1.[H][H]>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([NH2:19])[C:5]([NH2:18])=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 688437124-Fluoro-2-nitro-5-(3-piperidin-1-ylpropoxy)phenylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 688406714-Fluoro-5-(3-piperidin-1-ylpropoxy)benzene-1,2-diamineYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

200 mg of 4-fluoro-2-nitro-5-(3-piperidin-1-ylpropoxy)-phenylamine in solution in 15 mL of methanol are hydrogenated under 1 bar of hydrogen pressure in the presence of 20 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. 180 mg of 4-fluoro-5-(3-piperidin-1-ylpropoxy)benzene-1,2-diamine are obtained in the form of a black oil. The product 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-9eda14f292a04dc58a4cb9f659009c74
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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