Piperidine → 2-Nitro-4-fluoro-5-(piperidin-1-yl)aniline

HRID 1004573Notes

Reaction equation

HRID 1004573 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][CH2:19][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][CH2:19][CH2:18][CH2:17]2)=[CH:6][C:5]=1[NH2:12])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 14797Potassium HydroxideHCID 253877Potassium BromideHCID 2773811N-(5-chloro-4-fluoro-2-nitrophenyl)acetamide

Product 1

HCID 187927152-Nitro-4-fluoro-5-(piperidin-1-yl)anilineYield 52%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Nitro-4-fluoro-5-(piperidin-1-yl)aniline (13.0 g, 52%) was prepared by an analogous procedure as described in preparation 1 (step 3) using N-(2-nitro-4-fluoro-5-chloro phenyl)acetamide (25.0 g, 0.107 mol) (obtained in preparation 1, step 2), piperidine (45.8 a, 0.537 mol), potassium hydroxide (9.0 g, 0.16 mol) and dimethyl sulfoxide (100 mL). mp 112-113° C. IR (KBr) 3472, 1234 cm-1 ; 1H NMR (CDCl3) δ 1.60 (m, 2H, CH2), 1.70 (m, 4H, (CH2)2), 3.22 (m, 4H, N(CH2)2), 5.88 (d, J=7.6 Hz, 1H), 6.08 (brs, 2H, NH2), 7.78 (d, J=14.2 Hz, 1H) ; Mass (m/z) 239 (M+.).

Workup

  1. customas described in preparation 1 (step 3)

Sources & evidence

ORD record
ord-3c5c10fe06874fffa63dea60e6eff067
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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