1-(2-Methoxyphenyl)piperazine → HCID 44210117, compound

HRID 1034167Notes

Reaction equation

HRID 1034167 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:17][CH2:18][CH2:19][CH2:20][CH2:21]Cl)[C:9]([N+:23]([O-:25])=[O:24])=[C:8]([CH3:26])[NH:7][C:6]=1[NH2:27])=[O:4].[CH3:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.[I-].[Na+].C(=O)(O)[O-].[Na+]>C(O)(C)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:17][CH2:18][CH2:19][CH2:20][CH2:21][N:39]2[CH2:38][CH2:37][N:36]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[O:29][CH3:28])[CH2:41][CH2:40]2)[C:9]([N+:23]([O-:25])=[O:24])=[C:8]([CH3:26])[NH:7][C:6]=1[NH2:27])=[O:4]

Participants

6

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 70074769HCID 70074769, compound

Product 1

HCID 44210117HCID 44210117, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a 5 liter 4-neck round-bottom flask fitted with mechanical stirrer, reflux condenser and thermowell, under a nitrogen atmosphere, was added 37.87 g of 2-amino- 1,4-dihydro-4-(2-[(4-chlorobutyl)thio]phenyl)-6-methyl-5-nitro-3-pyridinecarboxylic acid methyl ester, 3.5 liters of isopropanol, 35.35 g of 1-(2-methoxyphenyl)piperazine, 27.57 g of sodium iodide and 15.45 g of sodium bicarbonate. The reaction mixture was heated at reflux for 6.5 hr., then stirred overnight at room temperature. The solvent was removed by rotary evaporation and the residue was partitioned between dichloromethane and water. The aqueous layer was washed with dichloromethane (2×300 ml), the organic layers combined, washed with water, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by column chromatography, eluting with 5% methanol in ethyl acetate. The product (Ex. No. 1, Table 1) was isolated as an orange solid, 37.23 g. 1H-NMR (d6 -DMSO) δ 1.60(m,4H); 2.33(m,2H); 2.40(s,3H); 2.45(m,4H); 2.92(m,6H); 3.43(s,3H); 3.76(s,3H); 5.59(s,1H); 6.73-6.95 (m,6H); 7.09(m,2H); 7.35(m,1H); 9.50(br s,1H). Mass spectrum: 568 (M+1).

Workup

  1. customTo a 5 liter 4-neck round-bottom flask fitted with mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 6.5 hr
  5. customThe solvent was removed by rotary evaporation
  6. customthe residue was partitioned between dichloromethane and water
  7. washThe aqueous layer was washed with dichloromethane (2×300 ml)
  8. washwashed with water
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe crude product was purified by column chromatography
  13. washeluting with 5% methanol in ethyl acetate
  14. custom1, Table 1) was isolated as an orange solid, 37.23 g

Sources & evidence

ORD record
ord-df08529671224a3e9ca8f8c057043ba3
Source dataset
uspto-grants-1994_05
Patent number
US05314887

Reaction notes

Loading…