1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-[(5,6-Dimethyl-2-methoxypyridin-3-yl)aminothiocarbonyl]-4-(3,5-dimethylphenyl)piperazine

HRID 377839Notes

Reaction equation

HRID 377839 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:11][C:12](=[S:20])OC2C=CC=CC=2)[C:5]([O:9][CH3:10])=[N:6][C:7]=1[CH3:8].[CH3:21][C:22]1[CH:23]=[C:24]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:25]=[C:26]([CH3:28])[CH:27]=1.C1CCN2C(=NCCC2)CC1>O1CCCC1>[CH3:1][C:2]1[CH:3]=[C:4]([NH:11][C:12]([N:32]2[CH2:33][CH2:34][N:29]([C:24]3[CH:25]=[C:26]([CH3:28])[CH:27]=[C:22]([CH3:21])[CH:23]=3)[CH2:30][CH2:31]2)=[S:20])[C:5]([O:9][CH3:10])=[N:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27586261-(3,5-Dimethylphenyl)piperazineHCID 53824458Phenyl N-(5,6-dimethyl-2-methoxypyridin-3-yl)thiocarbamate

Product 1

HCID 541191641-[(5,6-Dimethyl-2-methoxypyridin-3-yl)aminothiocarbonyl]-4-(3,5-dimethylphenyl)piperazineYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyl N-(5,6-dimethyl-2-methoxypyridin-3-yl)thiocarbamate(200 mg, 0.7 mmol) and 1-(3,5-dimethylphenyl)piperazine(154 mg 0.7 mmol) were dissolved in anhydrous tetrahydrofuran and DBU(106 mg) was added thereto. The mixture was stirred at room temperature for 2 hours and concentrated under the reduced pressure to remove the solvent. The concentrate was purified by column chromatography(ethylacetate:hexane=1:2) to obtain the titled compound.

Workup

  1. concentrationconcentrated under the reduced pressure
  2. customto remove the solvent
  3. customThe concentrate was purified by column chromatography(ethylacetate:hexane=1:2)

Sources & evidence

ORD record
ord-a8b9bb42ed6844189698de0682412016
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

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