HCID 602112, compound → 4-(Piperazin-1-yl)benzene-1,2-diamine

HRID 1004586Notes

Reaction equation

HRID 1004586 reaction equation
[N:1]1([C:7]2[CH:8]=[CH:9][C:10]([N+:14]([O-])=O)=[C:11]([CH:13]=2)[NH2:12])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1>C(O)C.[Pd]>[N:1]1([C:7]2[CH:8]=[CH:9][C:10]([NH2:14])=[C:11]([NH2:12])[CH:13]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 602112HCID 602112, compound

Product 1

HCID 133540674-(Piperazin-1-yl)benzene-1,2-diamineYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The nitroaniline derivative (10.0 g, 0.045 mol) (obtained in step 1 above) was hydrogenated using 10% Pd-C (1.5 g) in ethanol (45 mL), by an analogous procedure to that described in preparation 1 (step 4) to yield 4-(piperazin-1-yl)-1, 2-phenylenediamine (8.0 g, 93%) as a brown viscous oil. IR (Neat) 3342 cm-1 ; 1H NMR (CDCl3) δ 2.80 (brs, 5H, NH), 3.00 (m, 8H, 4×NCH2), 6.30 (d, J=8.2 Hz, 1H), 6.38 (s, 1H), 6.62 (d, J=8.0 Hz, 1H); Mass (m/z) 192 (M+.).

Workup

  1. customby an analogous procedure to that described in preparation 1 (step 4)

Sources & evidence

ORD record
ord-08e9c54b9bd849fb8aa7c9ce9bc067a5
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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