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

HRID 1638667Notes

Reaction equation

HRID 1638667 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-5daf0a2c72574547a0eebc1ad1923fa5
Source dataset
uspto-grants-1989_11
Patent number
US04880806

Reaction notes

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