HCID 68842884, compound → HCID 68842872, compound

HRID 2274404Notes

Reaction equation

HRID 2274404 reaction equation
[F:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:6][C:5]([NH2:19])=[C:4]([N+:20]([O-])=O)[CH:3]=1.[H][H]>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([NH2:20])[C:5]([NH2:19])=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 68842884HCID 68842884, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68842872HCID 68842872, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

758 mg of 4-fluoro-2-nitro-5-(4-piperidin-1-ylbutoxy)-phenylamine in solution in 40 mL of methanol are hydrogenated under 1 bar of hydrogen pressure in the presence of 75 mg of palladium-on-charcoal at 25° C. for 16 hours. The reaction crude is filtered through celite and the filtrate is concentrated under vacuum in a rotary evaporator. 670 mg of 4-fluoro-5-(4-piperidin-1-ylbutoxy)benzene-1,2-diamine are isolated in the form of a black oil. 1H NMR (300 MHz, DMSO-d6, δ in ppm): from 1.29 to 1.56 (m, 8H); 1.62 (m, 2H); from 2.20 to 2.32 (m, 6H); 3.82 (t, J=6.5 Hz, 2H); 4.27 (broad m, 4H); 6.32 (d, J=9.0 Hz, 1H); 6.34 (d, J=13.0 Hz, 1H).

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-f8f379f4e5b74baf8be76481c5463e82
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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