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

HRID 2391786노트

반응식

HRID 2391786 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 516892Sodium Bicarbonate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-04a9657e544b4d8e89db719794e0f50e
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273882B2

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