Triethylamine → Tert-butyl 4-(4-bromo-2-cyanophenyl)piperazine-1-carboxylate

HRID 2209167노트

반응식

HRID 2209167 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[C:7]#[N:8].[N:11]1([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(N(CC)CC)C>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:14]2[CH2:13][CH2:12][N:11]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15]2)=[C:6]([C:7]#[N:8])[CH:9]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27249005-Bromo-2-fluorobenzonitrile

생성물 1

HCID 56763808Tert-butyl 4-(4-bromo-2-cyanophenyl)piperazine-1-carboxylate수율 80%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

In a pressure tube, 5-bromo-2-fluorobenzonitrile (2500 mg, 12.5 mmol), tert-butyl piperazine-1-carboxylate (2444.45 mg, 13.12 mmol), triethylamine (5.23 ml, 37.5 mmol) in dimethylsulfoxide (10 ml) were combined and refluxed at 100 C for ovn. The mixture was cooled, and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was dried using sodium sulfate and concentrated. The residue was purified by flash column chromatography on silica gel 5-60% ethyl acetate/hexane to provide a light brown oil, tert-butyl 4-(4-bromo-2-cyanophenyl)piperazine-1-carboxylate (3660 mg, 80%).

후처리

  1. temperaturerefluxed at 100 C for ovn
  2. temperatureThe mixture was cooled
  3. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography on silica gel 5-60% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-f7aeb9dea80e4af889c73bab9a226e2c
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376441B2

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