Dimethylformamide → 1-[[(2-Ethoxy)ethyl]-1H-benzimidazol-2-yl][1-(t-butyloxycarbonyl)-4-piperidinyl)methanone

HRID 1769030노트

반응식

HRID 1769030 반응식
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)=[O:11].[CH2:25]([O:27][CH2:28][CH2:29]Br)[CH3:26].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:26][CH2:25][O:27][CH2:28][CH2:29][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]1)=[O:11]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 611412-Bromoethyl ethyl etherHCID 183332351-(t-butoxycarbonyl)-4-(1H-benzimidazole-2-carbonyl)piperidine

생성물 1

HCID 540144471-[[(2-Ethoxy)ethyl]-1H-benzimidazol-2-yl][1-(t-butyloxycarbonyl)-4-piperidinyl)methanone

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

Mix [1H-benzimidazol-2-yl][1-(t-butyloxycarbonyl)-4-piperidinyl]methanone (4.25 g, 12.91 mmol), 2-bromoethyl ethyl ether (2.34 g, 15.3 mmol), potassium carbonate (5.29 g, 38.25 mmol) and dimethylformamide (100 mL). Stir and heat and at 90° C. overnight. Allow to cool to room temperature, dilute with water and extract with ethyl acetate (2×). Wash the combined organic phases with water (3×), then brine and dry (MgSO4). Evaporate the solvent in vacuo and purify by chromatography to give the title compound.

후처리

  1. temperatureto cool to room temperature
  2. extractionextract with ethyl acetate (2×)
  3. washWash the combined organic phases with water (3×)
  4. dry with materialbrine and dry (MgSO4)
  5. customEvaporate the solvent in vacuo
  6. custompurify by chromatography

출처 및 근거

ORD 기록
ord-3e4334f1fbb148cabde94948c2351aba
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05380731

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