Piperazine → 2-Nitro-4-fluoro-5-(piperazin-1-yl)aniline

HRID 1004578Notes

Reaction equation

HRID 1004578 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([F:10])[C:7](Cl)=[CH:6][C:5]=1[NH:12]C(=O)C)([O-:3])=[O:2].[NH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.[OH-].[K+].[K+].[Br-]>CS(C)=O>[N+:1]([C:4]1[CH:9]=[C:8]([F:10])[C:7]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:6][C:5]=1[NH2:12])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 4837PiperazineHCID 14797Potassium HydroxideHCID 253877Potassium BromideHCID 2773811N-(5-chloro-4-fluoro-2-nitrophenyl)acetamide

Product 1

HCID 187927172-Nitro-4-fluoro-5-(piperazin-1-yl)anilineYield 77.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Nitro-4-fluoro-5-(piperazin-1-yl)aniline (5.6 g, 77%) was prepared by a procedure analogous to that described in preparation 1 (step 3) using N-(2-nitro-4-fluoro-5-chlorophenyl)acetamide (7.4 g, 0.03 mol) (obtained in preparation 1, step 2), piperazine (27.2 g, 0.3 mol), potassium hydroxide (2.5 g, 0.045 mol) and dimethyl sulfoxide (30 mL). mp 120-121° C.; IR (KBr) 3334, 1504, 1251 cm-1 ; 1H NMR (CDCl3 +CD3OD) δ 3.00 (t, J=5.4 Hz, 4H, N(CH2)2); 3.20 (t, J=5.6 Hz, 4H, N(CH2)2), 3.82 (brs, 3H, NH), 6.18 (d, J=8.2 Hz, 1H), 7.74 (d, J=13.8 Hz, 1H); Mass (m/z) 240 (M+.).

Workup

  1. customthat described in preparation 1 (step 3)

Sources & evidence

ORD record
ord-574ec1803649434388cdb1b2d0ed5fcf
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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