2-Nitro-4-fluoro-5-(piperidin-1-yl)aniline → 4-Fluoro-5-(piperidin-1-yl)-1,2-phenylenediamine

HRID 1004574Notes

Reaction equation

HRID 1004574 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([F:11])[C:8]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:7][C:5]=1[NH2:6])([O-])=O>C(O)C.[Pd]>[F:11][C:9]1[C:8]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:7][C:5]([NH2:6])=[C:4]([NH2:1])[CH:10]=1

Participants

4

Reactant 1

HCID 187927152-Nitro-4-fluoro-5-(piperidin-1-yl)aniline

Product 1

HCID 187927964-Fluoro-5-(piperidin-1-yl)-1,2-phenylenediamineYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The nitroaniline derivative (6.2 g, 0.026 mol) (obtained in step 1 above) was hydrogenated using 10% Pd-C (1.0 g,) in ethanol (30 mL), using an analogous procedure as described in preparation 1 (step 4) to yield 4-fluoro-5-(piperidin-1-yl)-1,2-phenylenediamine (5.3 g 98%) as brown viscous oil. IR (Neat) 3346 cm-1 ; 1H NMR (CDCl3) δ 1.54 (m, 2H, CH2), 1.70 (m, 4H, (CH2)2), 2.90 (m, 4H, N(CH2)2), 3.10 (brs, 4H, 2×NH2), 6.40 (d, J=8.8 Hz, 1H), 6.48 (d, J=13.8 Hz, 1H); Mass (m/z) 209 (M+.).

Workup

  1. customas described in preparation 1 (step 4)

Sources & evidence

ORD record
ord-886ce189265b47a288c437ce50d360e0
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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