1-Ethylpiperazine → 4-(4-Ethylpiperazin-1-yl)-6-(4-methoxyphenyl)thieno[3,2-c]pyridine

HRID 1251187Notes

Reaction equation

HRID 1251187 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:3]=1.[CH2:19]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[CH3:20]>>[CH2:19]([N:21]1[CH2:26][CH2:25][N:24]([C:2]2[C:7]3[CH:8]=[CH:9][S:10][C:6]=3[CH:5]=[C:4]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[N:3]=2)[CH2:23][CH2:22]1)[CH3:20]

Participants

3

Reactant 2

HCID 791961-EthylpiperazineHCID 225029374-Chloro-6-(4-methoxyphenyl)thieno[3,2-c]pyridine

Product 1

HCID 225028824-(4-Ethylpiperazin-1-yl)-6-(4-methoxyphenyl)thieno[3,2-c]pyridineYield 61.5%

Conditions

Temperature
130 °C

Procedure

A mixture of 4-chloro-6-(4-methoxyphenyl)thieno[3,2-c]pyridine (6.6 g) and N-ethylpiperazine (30 ml) was heated at 130° C. for 2 hr. The reaction mixture was evaporated, and to the resulting residue were added potassium carbonate and water. The resulting mixture was extracted with ethyl acetate, and the resulting organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was removed, and the resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give the title compound as a pale brown oil (5.2 g, yield; 61.5%).

Workup

  1. customThe reaction mixture was evaporated
  2. additionto the resulting residue were added potassium carbonate and water
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washthe resulting organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed
  7. customthe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-debf07c446e746ee96564959209792ff
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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