Hydrochloric Acid → HCID 22117357, compound

HRID 1275557Notes

Reaction equation

HRID 1275557 reaction equation
Cl.Cl.[Cl:3][CH2:4][CH2:5][CH2:6][S:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[C:9]=1[CH3:22].[CH2:23]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl>C(#N)C.O>[ClH:3].[CH2:23]([N:30]1[CH2:35][CH2:34][N:33]([CH2:4][CH2:5][CH2:6][S:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][S:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[C:9]=2[CH3:22])[CH2:32][CH2:31]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 759941-BenzylpiperazineHCID 22117318HCID 22117318, compound

Product 1

HCID 22117357HCID 22117357, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

4-(3-Chloropropylthio)-3-methyl-2-[(2-pyridinylthio)methyl]-pyridine dihydrochloride (0.59 g; 1.5 mmol) is stirred at 100° C. for 24 h in acetonitrile (10 ml) with benzylpiperazine (2.0 mmol) with addition of potassium carbonate (7.5 mmol) and catalytic amounts of sodium iodide. After addition of water, the mixture is extracted with dichloromethane (2×10 ml), the combined organic phases are washed with water, dried and concentrated, and the crude product (yellow oil) is chromatographed on silica gel. The pure product fractions are combined, concentrated, dissolved in ethanol and treated with 3.5 equivalents of conc. hydrochloric acid. The precipitated solid is filtered off, washed with diisopropyl ether and dried. The title compound is obtained as colorless crystals; m.p. 170-172° C.; yield 81% of theory.

Workup

  1. extractionthe mixture is extracted with dichloromethane (2×10 ml)
  2. washthe combined organic phases are washed with water
  3. customdried
  4. concentrationconcentrated
  5. customthe crude product (yellow oil) is chromatographed on silica gel
  6. concentrationconcentrated
  7. dissolutiondissolved in ethanol
  8. filtrationThe precipitated solid is filtered off
  9. washwashed with diisopropyl ether
  10. customdried

Sources & evidence

ORD record
ord-c71a8936287b4758bd6970c7ff26995b
Source dataset
uspto-grants-2000_12
Patent number
US06162809

Reaction notes

Loading…