N6-((4-Fluorophenyl)methyl)-3-nitropyridine-2,6-diamine → N~6~-[(4-Fluorophenyl)methyl]pyridine-2,3,6-triamine

HRID 619676Notes

Reaction equation

HRID 619676 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[N:3]=1.[H][H]>COCCO.[Ni]>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[N:3]=1

Participants

5

Reactant 2

HCID 118472N6-((4-Fluorophenyl)methyl)-3-nitropyridine-2,6-diamineHCID 178418361HCID 178418361, compound

Product 1

HCID 10868158N~6~-[(4-Fluorophenyl)methyl]pyridine-2,3,6-triamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 80192-MethoxyethanolSolvent

Procedure

2-amino-3-nitro-6-(4-fluorobenzylamino)pyridine (ANFP) is dissolved in 2-methoxyethanol and is hydrogenated with hydrogen in the presence of Raney nickel at 5 bar and 60° C. to give 2,3-diamino-6-(4-fluorobenzyl-amino)pyridine. This is acylated with ethyl chloroformate and triethylamine under inert gas to give flupirtine base. The catalyst is filtered off and a solution of isopropanol and maleic acid is added directly to the filtrate which contains triethylamine hydrochloride, crude flupirtine maleate being precipitated with vigorous stirring under an inert-gas atmosphere.

Sources & evidence

ORD record
ord-3b7372a6373a49299bbb1fde1f609d6c
Source dataset
uspto-grants-1999_09
Patent number
US05959115

Reaction notes

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