Cesium carbonate → 1-(4-Methoxy-benzyl)-2,2-dimethyl-4-(5-nitro-pyridin-2-ylmethyl)-piperazine

HRID 1189835Notes

Reaction equation

HRID 1189835 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10]OS(C)(=O)=O)=[N:8][CH:9]=1)([O-:3])=[O:2].[CH3:16][O:17][C:18]1[CH:32]=[CH:31][C:21]([CH2:22][N:23]2[CH2:28][CH2:27][NH:26][CH2:25][C:24]2([CH3:30])[CH3:29])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:22][N:23]2[CH2:28][CH2:27][N:26]([CH2:10][C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=3)[CH2:25][C:24]2([CH3:30])[CH3:29])=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 635966481-(4-Methoxy-benzyl)-2,2-dimethyl-piperazineHCID 86641144Methanesulfonic acid 5-nitro-pyridin-2-ylmethyl ester

Product 1

HCID 669145841-(4-Methoxy-benzyl)-2,2-dimethyl-4-(5-nitro-pyridin-2-ylmethyl)-piperazineYield 80.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methanesulfonic acid 5-nitro-pyridin-2-ylmethyl ester (Step 112.3) (0.5 g, 2.16 mmol), 1-(4-methoxy-benzyl)-2,2-dimethyl-piperazine (Step 108.2) (0.655 g, 2.8 mmol, 1.3 equiv), cesium carbonate (0.845 g, 2.6 mmol, 1.2 equiv), and DMF (4 ml) was stirred for 5 h at rt, quenched by addition of a saturated aqueous solution of NaHCO3 and extracted with EtOAc. The organic phase was washed with a saturated aqueous solution of NaHCO3, dried (Na2SO4), filtered and concentrated. The residue was purified by by silica gel column chromatography (DCM DCM/MeOH, 99:1) to provide 0.642 g of the title compound as a red solid: ESI-MS: 371.2 [M+H]+; tR=3.18 min (System 1); TLC: Rf=0.44 (DCM/MeOH, 9:1).

Workup

  1. customquenched by addition of a saturated aqueous solution of NaHCO3
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with a saturated aqueous solution of NaHCO3
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by by silica gel column chromatography (DCM DCM/MeOH, 99:1)

Sources & evidence

ORD record
ord-e35c871467334d6bbf7dcefb1a9a9ec3
Source dataset
uspto-grants-2014_03
Patent number
US08674099B2

Reaction notes

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