Potassium Carbonate → 2-Chloro-3-[2-ethyl-4-(phenylmethyl)-1-piperazinyl]pyrazine

HRID 991671Notes

Reaction equation

HRID 991671 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1.[CH2:9]([N:16]1[CH2:21][CH2:20][NH:19][CH:18]([CH2:22][CH3:23])[CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:9]([N:16]1[CH2:21][CH2:20][N:19]([C:2]2[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=2)[CH:18]([CH2:22][CH3:23])[CH2:17]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 785752,3-DichloropyrazineHCID 220365411-Benzyl-3-ethylpiperazine

Product 1

HCID 220363902-Chloro-3-[2-ethyl-4-(phenylmethyl)-1-piperazinyl]pyrazineYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,3-dichloropyrazine (3.9 g, 27 mmol), 1-benzyl-3-ethylpiperazine (4.6 g, 22.5 mmol; from Step 1) and K2CO3 (6.2 g, 45 mmol) in DMF (10 mL) was stirred at 100° C. for 4 days. The solvent from the filtered reaction mixture was evaporated off and the residue was purified by column chromatography on silica using heptane/EtOAc (90:10) as eluent to yield 5.0 g (71%) of the title compound as a light yellow oil. HRMS m/z calcd for C17H21ClN4 (M)+ 316.1455, found 316.1448.

Workup

  1. customThe solvent from the filtered reaction mixture
  2. customwas evaporated off
  3. customthe residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-e489cca6207c4706a9cad9133db08e9b
Source dataset
uspto-grants-2002_10
Patent number
US06465467B1

Reaction notes

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