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

HRID 1189758ノート

反応式

HRID 1189758 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 516892Sodium Bicarbonate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b150e861ec7c45aabb2a49e2ef6cb47c
出典データセット
uspto-grants-2014_03
特許番号
US08674099B2

反応ノート

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