Sodium hydride → Tert-butyl [4-[2-(benzimidazol-2-yloxy)ethyl]piperazin-1-yl] carboxylate

HRID 1064874노트

반응식

HRID 1064874 반응식
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[H-].[Na+].C([N:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N:28]=[C:27]1Cl)C1C=CC=CC=1>CN(C=O)C>[N:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[NH:28][C:27]=1[O:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 735736Tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylateHCID 38219871-Benzyl-2-chlorobenzimidazole

생성물 1

HCID 86591243Tert-butyl [4-[2-(benzimidazol-2-yloxy)ethyl]piperazin-1-yl] carboxylate수율 106.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
75 °C

실험 절차

To a solution of tert-butyl 4-(2-hydroxyethyl)-1-piperazinecarboxylate (230 mg, 1.00 mmol) in DMF (2 ml) was added sodium hydride (55%, 52 mg, 1.19 mmol) with ice-cooling and stirred at 75° C. for 30 minutes, and then added 1-benzyl-2-chlorobenzimidazole (243 mg, 1.00 mmol) and stirred at 75° C. for 24 hours. The reaction solution was concentrated in vacuo, and the resulting residue was dissolved in chloroform. The organic layer was washed with water and a saturated sodium chloride solution successively, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (silica gel 25 g, developing solvent; hexane:ethyl acetate=5:1 1:1) to provide 369 mg (yield 85%) of tert-butyl [4-[2-(benzimidazol-2-yloxy)ethyl]piperazin-1-yl]carboxylate as colorless solid.

후처리

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated in vacuo
  3. dissolutionthe resulting residue was dissolved in chloroform
  4. washThe organic layer was washed with water
  5. dry with materiala saturated sodium chloride solution successively, dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by a silica gel column chromatography (silica gel 25 g, developing solvent; hexane:ethyl acetate=5:1 1:1)

출처 및 근거

ORD 기록
ord-865c64db3c5743e4beb6ef167e1fd6c3
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06969711B2

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