Sodium hydride → 4-(2-Methoxy-ethoxy)-1-(3-methoxy-4-nitro-phenyl)-piperidine

HRID 2424390노트

반응식

HRID 2424390 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[H-].[Na+].[CH3:21][O:22][CH2:23][CH2:24]Br.[Cl-].[NH4+]>CN(C)C=O.O>[CH3:21][O:22][CH2:23][CH2:24][O:18][CH:15]1[CH2:16][CH2:17][N:12]([C:5]2[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:13][CH2:14]1

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 809722-Bromoethyl methyl etherHCID 259188601-(3-Methoxy-4-nitrophenyl)piperidin-4-ol

생성물 1

HCID 587485624-(2-Methoxy-ethoxy)-1-(3-methoxy-4-nitro-phenyl)-piperidine수율 29.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 1-(3-Methoxy-4-nitro-phenyl)-piperidin-4-ol (300 mg, 1.2 mmol) in N,N-dimethylformamide (3.0 mL), sodium hydride (1.52 g, 3.8 mmol) is added. After stirring, 2-bromoethyl methyl ether (150 μl, 1.6 mmol) is added and the mixture is further stirred at 70° C. for 15 hours. After addition of saturated aqueous ammonium chloride, the mixture is poured into water and extracted twice with ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue is purified by silica gel column chromatography (n-hexane-ethyl acetate gradient) to afford 4-(2-Methoxy-ethoxy)-1-(3-methoxy-4-nitro-phenyl)-piperidine (111 mg, 29%) as a yellow oil.

후처리

  1. stirringthe mixture is further stirred at 70° C. for 15 hours
  2. extractionextracted twice with ethyl acetate
  3. washThe organic layer is washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue is purified by silica gel column chromatography (n-hexane-ethyl acetate gradient)

출처 및 근거

ORD 기록
ord-e1b6a81cbde244229d48ff4ce5da4c58
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07964592B2

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