Potassium Carbonate → 4-(((2R)-1,4-dibenzyl-2-piperazinyl)methyl)-3-(1-methylethyl)-2-piperazinone

HRID 1972560Notes

Reaction equation

CS(O[CH2:6][C@H:7]1[CH2:12][N:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9][N:8]1[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=O)=O.[CH:27]([CH:30]1[NH:35][CH2:34][CH2:33][NH:32][C:31]1=[O:36])([CH3:29])[CH3:28].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CCOC(C)=O>[CH2:20]([N:8]1[CH2:9][CH2:10][N:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:12][C@@H:7]1[CH2:6][N:35]1[CH2:34][CH2:33][NH:32][C:31](=[O:36])[CH:30]1[CH:27]([CH3:29])[CH3:28])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 130 °C

Procedure

((2R)-1,4-dibenzyl-2-piperazinyl)methyl methanesulfonate (0.450 g, 1.202 mmol) was combined with 3-isopropylpiperazin-2-one (0.179 g, 1.262 mmol, ChemBridge, San Diego, Calif.) and potassium carbonate (0.498 g, 3.60 mmol, Sigma-Aldrich, St. Louis, Mo.) in acetonitrile (5.46 mL) and heated at 130° C. After 1 h, the mixture was diluted with EtOAc and the solids were removed by filtering through a 0.2 μm millipore Millex-FG filter (Millipore, Billerica, Mass.). After concentration, the crude residue was purified by silica gel chromatography (2.5-8.5% MeOH in CH2Cl2) to give 4-(((2R)-1,4-dibenzyl-2-piperazinyl)methyl)-3-(1-methylethyl)-2-piperazinone (212 mg).

Workup

customthe solids were removed
filtrationby filtering through a 0.2 μm
filtrationmillipore Millex-FG filter (Millipore, Billerica, Mass.)
concentrationAfter concentration
customthe crude residue was purified by silica gel chromatography (2.5-8.5% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-88687cedb27a454d9ecbdf490a6c9eaa
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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