Potassium Carbonate → HCID 62492717, compound

HRID 885856Notes

Reaction equation

HRID 885856 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[C:7]#[N:8].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:3]=[CH:4][C:5]([N:21]2[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][CH2:20]2)=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 936535-Chloro-2-fluorobenzonitrile

Product 1

HCID 62492717HCID 62492717, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-chloro-2-fluoro-benzonitrile (500 mg, 3.21 mmol), K2CO3 (1.32 g, 9.64 mmol) and 1-methyl-piperazine (482 mg, 4.81 mmol) in DMSO (6.4 ml) was stirred at 100° C. for 6 h and then partitioned between water and Et2O. The organic phase was dried over Na2SO4 and evaporated in vacuo. The crude mixture was purified by column chromatography (eluent: DCM/MeOH/NH4OH 98:2:0.1) to give 660 mg of 5-chloro-2-(4-methyl-piperazin-1-yl)-benzonitrile.

Workup

  1. custompartitioned between water and Et2O
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated in vacuo
  4. customThe crude mixture was purified by column chromatography (eluent: DCM/MeOH/NH4OH 98:2:0.1)

Sources & evidence

ORD record
ord-4fe1e890755840498bd57785e6826982
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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