2-Chloro-5-nitropyridine → tert-Butyl 4-(5-nitropyridin-2-yl)piperazine-1-carboxylate

HRID 55870Notes

Reaction equation

HRID 55870 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>CC#N>[C:14]([O:13][C:11]([N:18]1[CH2:23][CH2:22][N:21]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH2:20][CH2:19]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

4

Reactant 2

HCID 783082-Chloro-5-nitropyridineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 16217943tert-Butyl 4-(5-nitropyridin-2-yl)piperazine-1-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
140 °C

Procedure

5-Nitro-2-chloropyridine (21) (350 mg, 2.21 mmol) and 1-Boc-piperazine (430 mg, 2.31 mmol) were dissolved in MeCN (3.6 mL). TEA (400 μL, 2.87 mmol) was added and the mixture heated at 140° C. in the microwave (250 W, stirring) for 30 minutes. The solvent was evaporated in vacuo and the residue dissolved in DCM (75 mL). The solution was washed with 0.5N HCl (2×20 mL) and the organic phase washed with saturated brine solution (40 mL), then dried (MgSO4), filtered and the solvent evaporated in vacuo to afford the title compound as a yellow solid (646 mg, 95%); LCMS, Rt=2.97 min (MeOH-FA method), m/z 309 (MH+).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue dissolved in DCM (75 mL)
  3. washThe solution was washed with 0.5N HCl (2×20 mL)
  4. washthe organic phase washed with saturated brine solution (40 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-2ca519e1a79944568638e5112ae5e11e
Source dataset
uspto-grants-2016_09
Patent number
US09433622B2

Reaction notes

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