Dimethyl Sulfide → 1-(2,2-Dimethyl-propyl)-4-(6-nitro-pyridin-3-yl)-piperazine

HRID 1910785Notes

Reaction equation

HRID 1910785 reaction equation
[CH3:1][C:2]([CH3:21])([CH3:20])[C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:12]=[N:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)[CH2:7][CH2:6]1)=O.CSC>C1COCC1>[CH3:1][C:2]([CH3:21])([CH3:20])[CH2:3][N:5]1[CH2:6][CH2:7][N:8]([C:11]2[CH:12]=[N:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 285264742,2-Dimethyl-1-[4-(6-nitro-pyridin-3-yl)-piperazin-1-yl]-propan-1-one

Product 1

HCID 671064301-(2,2-Dimethyl-propyl)-4-(6-nitro-pyridin-3-yl)-piperazineYield 52.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,2-dimethyl-1-[4-(6-nitro-pyridin-3-yl)-piperazin-1-yl]-propan-1-one (1.0 g, 3.42 mmol) in THF (10 mL) was added BH3.DMS (0.6 mL, 6.84 mmol) at r.t. and the reaction was then heated to reflux for 6 h. The reaction was cooled, quenched with ammonium chloride solution and extracted with ethyl acetate. The combined organic layers were washed with brine solution, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The crude material was purified by column chromatography over silica gel (60-120 mesh) using 20% ethyl acetate/petroleum ether as eluent to afford 1-(2,2-dimethyl-propyl)-4-(6-nitro-pyridin-3-yl)-piperazine (0.5 g, 52.5%).

Workup

  1. temperatureto reflux for 6 h
  2. temperatureThe reaction was cooled
  3. customquenched with ammonium chloride solution
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with brine solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe crude material was purified by column chromatography over silica gel (60-120 mesh)

Sources & evidence

ORD record
ord-9efe5cb69f37433089ca071eca603bfb
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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