Potassium Carbonate → HCID 67049738, compound

HRID 885859Notes

Reaction equation

HRID 885859 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:7](F)=[CH:6][C:3]=1[C:4]#[N:5].C([O-])([O-])=O.[K+].[K+].[CH3:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>CS(C)=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([N:21]2[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][CH2:20]2)=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-Methylpiperazine2×HCID 936562-Chloro-5-fluorobenzonitrile

Product 1

HCID 67049738HCID 67049738, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-5-fluoro-benzonitrile (1 g, 6.43 mmol), K2CO3 (2.66 g, 19.3 mmol) and 1-methyl-piperazine (1.02 g, 10.26 mmol) in DMSO (14 ml) was stirred at 100° C. overnight and then further 1-methyl-piperazine (1.02 g, 10.26 mmol) was added. The mixture was stirred at 100° C. overnight and then partitioned between water and Et2O. The organic phase was extracted with 1 M HCl and the aqueous layer was brought to basic conditions with NH4OH and extracted with DCM. The organic phase was dried over Na2SO4 and evaporated in vacuo to give 1 g of 2-chloro-5-(4-methyl-piperazin-1-yl)-benzonitrile.

Workup

  1. stirringThe mixture was stirred at 100° C. overnight
  2. custompartitioned between water and Et2O
  3. extractionThe organic phase was extracted with 1 M HCl
  4. extractionextracted with DCM
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-0455f541f6644fd7b987ed7dee78cf43
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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