1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-[(2-Methylquinolin-3-yl)aminothiocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine

HRID 377901Notes

Reaction equation

HRID 377901 reaction equation
[CH3:1][C:2]1[C:11]([NH:12][C:13](=[S:21])OC2C=CC=CC=2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH:27]=[C:28]([O:30][CH3:31])[CH:29]=1.C1CCN2C(=NCCC2)CC1>O1CCCC1>[CH3:1][C:2]1[C:11]([NH:12][C:13]([N:35]2[CH2:34][CH2:33][N:32]([C:26]3[CH:25]=[C:24]([O:23][CH3:22])[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=3)[CH2:37][CH2:36]2)=[S:21])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27362051-(3,5-Dimethoxyphenyl)piperazineHCID 53717370Phenyl N-(2-methylquinolin-3-yl)thiocarbamate

Product 1

HCID 545019501-[(2-Methylquinolin-3-yl)aminothiocarbonyl]-4-(3,5-dimethoxyphenyl)piperazineYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyl N-(2-methylquinolin-3-yl)thiocarbamate(147 mg, 0.5 mmol) and 1-(3,5-dimethoxyphenyl)piperazine(112 mg, 0.5 mmol) were dissolved in anhydrous tetrahydrofuran and DBU(117 mg, 0.75 mmol) was added and then the mixture was stirred at room temperature for 2 hrs. The above solution was concentrated under the reduced pressure to remove tetrahydrofuran and purified by column chromatography(ethylacetate:hexane=1:2) to obtain the titled compound.

Workup

  1. concentrationThe above solution was concentrated under the reduced pressure
  2. customto remove tetrahydrofuran
  3. custompurified by column chromatography(ethylacetate:hexane=1:2)

Sources & evidence

ORD record
ord-1b632425448e4240b8bdf8c9941e5b64
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

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