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

HRID 377887Notes

Reaction equation

HRID 377887 reaction equation
[CH3:1][O:2][C:3]1[C:12]([NH:13][C:14](=[S:22])OC2C=CC=CC=2)=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH:28]=[C:29]([O:31][CH3:32])[CH:30]=1.C1CCN2C(=NCCC2)CC1>O1CCCC1>[CH3:1][O:2][C:3]1[C:12]([NH:13][C:14]([N:36]2[CH2:35][CH2:34][N:33]([C:27]3[CH:26]=[C:25]([O:24][CH3:23])[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=3)[CH2:38][CH2:37]2)=[S:22])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27362051-(3,5-Dimethoxyphenyl)piperazineHCID 54112042Phenyl N-(2-methoxyquinolin-3-yl)thiocarbamate

Product 1

HCID 538540891-[(2-Methoxyquinolin-3-yl)aminothiocarbonyl]-4-(3,5-dimethoxyphenyl)piperazineYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyl N-(2-methoxyquinolin-3-yl)thiocarbamate(56 mg, 0.5 mmol) and 1-(3,5-dimethoxyphenyl)piperazine(111 mg, 0.5 mmol) were dissolved in anhydrous tetrahydrofuran and DBU(117 mg, 0.75 mmol) was added. The reaction solution was stirred at room temperature for 2 hours. The above solution was concentrated under the reduced pressure to remove tetrahydrofuran and concentrated was purified by column chromatography(Hexane:ether=5:1) to obtain the titled compound.

Workup

  1. concentrationThe above solution was concentrated under the reduced pressure
  2. customto remove tetrahydrofuran
  3. concentrationconcentrated
  4. customwas purified by column chromatography(Hexane:ether=5:1)

Sources & evidence

ORD record
ord-d7b91fe8e7464e43a8054ec3ecd4ff49
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

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