1-Methylpiperazine → 1-Methyl-4-(5-nitropyridin-2-yl)piperazine

HRID 2236523Notes

Reaction equation

HRID 2236523 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>ClCCl>[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 782402-Bromo-5-nitropyridine

Product 1

HCID 27640661-Methyl-4-(5-nitropyridin-2-yl)piperazineYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An amount of 2 g (9.85 mmol) of 2-bromo-5-nitro-pyridin is stirred in dichloromethane (50 mL), followed by addition of 1-methylpiperazine (10.9 mL, 98.5 mmol). The reaction mixture is refluxed for 1 h. After cooling, the mixture is extracted 3× with sodium bicarbonate, followed by additional washing with brine, dried over sodium sulfate, evaporated, to afford 2 g (91% yield) of yellow crystals; mp 75-76° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 1 h
  2. temperatureAfter cooling
  3. extractionthe mixture is extracted 3× with sodium bicarbonate
  4. washby additional washing with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-01de77ac1cd54dcc808e4beb358587e2
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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