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

HRID 1820622Notes

Reaction equation

HRID 1820622 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].C1CCN2C(=NCCC2)CC1>CN(C=O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].C(OCC)(=O)C>[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

7

Reactant 3

HCID 783082-Chloro-5-nitropyridineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 16217943tert-Butyl 4-(5-nitropyridin-2-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-chloro-5-nitropyridine (1.58 g, 10.0 mmol) in DMF (15 mL) was treated with 1-Boc-piperazine (1.96 g, 10.5 mmol) in the presence of DBU (3 mL) and Bu4NI (0.185 g, 0.5 mmol) at 80° C. for 18 h. The reaction mixture was diluted with ethyl acetate at 25° C. The organic phase was washed with H2O, saturated NaCl, dried over MgSO4 and then concentrated in vacuo to afford 4(5-nitropyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester as a yellow solid which was used for next step reaction without further purification. MS (ES+) m/z 309.4 (M+1).

Workup

  1. washThe organic phase was washed with H2O, saturated NaCl
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2d10dcf8142247f4a82d6391ceda3cce
Source dataset
uspto-grants-2009_10
Patent number
US07605161B2

Reaction notes

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