1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-[(2-Methoxynaphth-3-yl)aminocarbonyl]-4-(3,5-dimethylphenyl)piperazine

HRID 1841504Notes

Reaction equation

HRID 1841504 reaction equation
[CH3:1][O:2][C:3]1[C:12]([NH:13][C:14](=[O:22])OC2C=CC=CC=2)=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[CH3:23][C:24]1[CH:25]=[C:26]([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH:27]=[C:28]([CH3:30])[CH:29]=1.C1CCN2C(=NCCC2)CC1>O1CCCC1>[CH3:1][O:2][C:3]1[C:12]([NH:13][C:14]([N:34]2[CH2:35][CH2:36][N:31]([C:26]3[CH:27]=[C:28]([CH3:30])[CH:29]=[C:24]([CH3:23])[CH:25]=3)[CH2:32][CH2:33]2)=[O:22])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27586261-(3,5-Dimethylphenyl)piperazineHCID 23446160Phenyl N-(2-methoxynaphth-3-yl)carbamate

Product 1

HCID 234462211-[(2-Methoxynaphth-3-yl)aminocarbonyl]-4-(3,5-dimethylphenyl)piperazineYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyl N-(2-methoxynaphth-3-yl)carbamate (375 mg, 1.28 mmol) and 1-(3,5-dimethylphenyl)piperazine (208 mg, 1.28 mmol) were dissolved in anhydrous tetrahydrofuran (25 ml) and thereto DBU (195 mg, 1.28 mmol) was added, and then stirred at room temperature for 2 hours, concentrated under the reduced pressure to remove the solvent and purified by column chromatography to obtain the titled compound.

Workup

  1. concentrationconcentrated under the reduced pressure
  2. customto remove the solvent
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-1f5b9534f63248cea2238558cb4e3629
Source dataset
uspto-grants-2004_01
Patent number
US06683184B2

Reaction notes

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