Potassium Carbonate → 4-[3-(4-Benzyl-1-piperazinyl)propylthio]-3-methyl-2-[(4-pyridinylthio)methyl]pyridine

HRID 1275560Notes

Reaction equation

HRID 1275560 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([CH2:12][S:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[C:7]=1[CH3:20].[CH2:21]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:21]([N:28]1[CH2:33][CH2:32][N:31]([CH2:2][CH2:3][CH2:4][S:5][C:6]2[CH:11]=[CH:10][N:9]=[C:8]([CH2:12][S:13][C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[C:7]=2[CH3:20])[CH2:30][CH2:29]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 759941-BenzylpiperazineHCID 221173024-(3-Chloropropylthio)-3-methyl-2-[(4-pyridinylthio)methyl]pyridine

Product 1

HCID 221173144-[3-(4-Benzyl-1-piperazinyl)propylthio]-3-methyl-2-[(4-pyridinylthio)methyl]pyridineYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

According to the procedure indicated in Example 7, reaction of 4-(3-chloropropylthio)-3-methyl-2-[(4-pyridinylthio)methyl]pyridine with 1-benzylpiperazine and potassium carbonate in acetonitrile, after chromatography on silica gel and crystallization of the concentrated pure fraction from diisopropyl ether, gives the title compound as a colorless solid; m.p. 79-81° C.; yield 57% of theory. A hydrated hydrochloride can be prepared from isopropanol; m.p. 165° C. (dec.); yield 87% of theory.

Workup

  1. customafter chromatography on silica gel and crystallization of the concentrated pure fraction from diisopropyl ether

Sources & evidence

ORD record
ord-8266694c2c4b401bafd500bda0c1364b
Source dataset
uspto-grants-2000_12
Patent number
US06162809

Reaction notes

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