1-Methylpiperazine → 1-Methyl-4-(5-nitro-pyridin-2-ylmethyl)-piperazine

HRID 43073Notes

Reaction equation

HRID 43073 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[N+:15]([C:18]1[CH:19]=[CH:20][C:21]([CH:24]=O)=[N:22][CH:23]=1)([O-:17])=[O:16].[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:26][N:27]1[CH2:32][CH2:31][N:30]([CH2:24][C:21]2[CH:20]=[CH:19][C:18]([N+:15]([O-:17])=[O:16])=[CH:23][N:22]=2)[CH2:29][CH2:28]1

Participants

6

Reactant 3

HCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 151455015-Nitropyridine-2-carbaldehyde

Product 1

HCID 669146521-Methyl-4-(5-nitro-pyridin-2-ylmethyl)-piperazineYield 68.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

Sodium triacetoxyborohydride (1.4 g, 6.6 mmol, 2 equiv) was added portionwise to a cold (5° C.) solution of 5-nitro-pyridine-2-carbaldehyde (Step 39.3) (0.5 g, 3.3 mmol) and N-methyl-piperazine (0.4 mL, 3.6 mmol, 1.1 equiv) in DCM (10 mL). The reaction mixture was allowed to warm to rt, stirred for 16 h, diluted with DCM and saturated solution of NaHCO3, and extracted with DCM. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 91:8:1) to provide 0.532 g of the title compound as a yellow solid: ESI-MS: 237.2 [M+H]+; TLC: Rf=0.31 (DCM/MeOH/NH3aq, 91:8:1).

Workup

  1. extractionextracted with DCM
  2. washThe organic phase was washed with H2O and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 91:8:1)

Sources & evidence

ORD record
ord-539cbdd5fa7c41e2a29e0788ebbf4dc1
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

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