1-(2-Methoxyphenyl)piperazine → 1-[(5-Ethyl-2-methoxy-6-methylpyridin-3-yl)aminocarbonyl]-4-(2-methoxyphenyl)piperazine

HRID 1956188Notes

Reaction equation

HRID 1956188 reaction equation
C1(O[C:8](=[O:21])[NH:9][C:10]2[C:11]([O:19][CH3:20])=[N:12][C:13]([CH3:18])=[C:14]([CH2:16][CH3:17])[CH:15]=2)C=CC=CC=1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.C1CCN2C(=NCCC2)CC1>O1CCCC1>[CH2:16]([C:14]1[CH:15]=[C:10]([NH:9][C:8]([N:33]2[CH2:32][CH2:31][N:30]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[O:23][CH3:22])[CH2:35][CH2:34]2)=[O:21])[C:11]([O:19][CH3:20])=[N:12][C:13]=1[CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 19357010Phenyl N-(5-ethyl-2-methoxy-6-methylpyridin-3-yl)carbamate

Product 1

HCID 186630861-[(5-Ethyl-2-methoxy-6-methylpyridin-3-yl)aminocarbonyl]-4-(2-methoxyphenyl)piperazineYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyl-N-(5-ethyl-2-methoxy-6-methylpyridin-3-yl)carbamate(0.29 g, 1.0 mmol) and 1-(2-methoxyphenyl)piperazine(0.19 g, 1.0 mmol) were dissolved in tetrahydrofuran(10 ml) and DBU(0.15 g, 1.0 mol) was added thereto and the mixture was stirred at room temperature for 2 hours. Then, the reaction mixture was concentrated and chromatographed to obtain 0.33 g of the titled compound.

Workup

  1. concentrationThen, the reaction mixture was concentrated
  2. customchromatographed

Sources & evidence

ORD record
ord-93efa274d25f4f39a7d469a8bb3708d3
Source dataset
uspto-grants-1998_07
Patent number
US05780472

Reaction notes

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