Hydrochloric Acid → 2-(4-Ethoxycarbonyl-1-piperazinyl)-3,6-difluoro-5-nitrotoluene

HRID 1722285Notes

Reaction equation

HRID 1722285 reaction equation
[F:1][C:2]1[C:3]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:16][CH2:15]2)=[C:4]([C:7]([F:13])=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)[CH2:5]Cl.B.[Na].Cl>CS(C)=O>[CH2:23]([O:22][C:20]([N:17]1[CH2:18][CH2:19][N:14]([C:3]2[C:2]([F:1])=[CH:9][C:8]([N+:10]([O-:12])=[O:11])=[C:7]([F:13])[C:4]=2[CH3:5])[CH2:15][CH2:16]1)=[O:21])[CH3:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 156318302-(4-Ethoxycarbonyl-1-piperazinyl)-3,6-difluoro-5-nitrobenzyl chlorideHCID 178418435HCID 178418435, compound

Product 1

HCID 156318312-(4-Ethoxycarbonyl-1-piperazinyl)-3,6-difluoro-5-nitrotolueneYield 96.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3,6-difluoro-2-(4-ethoxycarbonyl-1-piperazinyl)-5-nitrobenzyl chloride (8.1 g) in dimethylsulfoxide (90 ml) is added gradually sodium boron hydride (1.8 g) at below 30° C. The mixture is stirred at the same temperature for one hour, and the reaction mixture is poured into ice water, and then acidified with conc. hydrochloric acid and extracted with diethyl ether. The solvent is distilled off to give 2-(4-ethoxycarbonyl-1-piperazinyl)-3,6-difluoro-5-nitrotoluene (7.1 g).

Workup

  1. extractionextracted with diethyl ether
  2. distillationThe solvent is distilled off

Sources & evidence

ORD record
ord-978ccbe7bf5342e4a4355369103d4acf
Source dataset
uspto-grants-1989_08
Patent number
US04855292

Reaction notes

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