Diisopropylethylamine → 4-(8-Azabicyclo[3.2.1]oct-8-yl)-3-(trifluoromethyl)benzonitrile

HRID 586078노트

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HRID 586078 반응식
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].Cl.[CH:15]12[NH:22][CH:19]([CH2:20][CH2:21]1)[CH2:18][CH2:17][CH2:16]2.C(N(CC)C(C)C)(C)C>CS(C)=O>[CH:19]12[N:22]([C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=3[C:10]([F:13])([F:12])[F:11])[CH:15]([CH2:21][CH2:20]1)[CH2:16][CH2:17][CH2:18]2

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 1442554-Fluoro-3-(trifluoromethyl)benzonitrileHCID 5222728-Azabicyclo[3.2.1]octane hydrochloride

생성물 1

HCID 223376664-(8-Azabicyclo[3.2.1]oct-8-yl)-3-(trifluoromethyl)benzonitrile

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
120 °C

실험 절차

4-Fluoro-3-(trifluoromethyl)benzonitrile (1.35 g, 7.14 mmol), 8-aza-bicyclo[3.2.1]octane hydrochloride (1.26 g, 8.57 mmol), and N,N-diisopropylethylamine (1.79 g, 13.8 mmol) were combined in DMSO (15 mL) and heated at 120° C. for 24 hours. The mixture was allowed to cool to ambient temperature and partitioned between diethyl ether and saturated NaHCO3 solution. The separated aqueous phase was extracted with diethyl ether and the combined organic layers were washed with water, brine, dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure to provide the title compound which was used in the next step without further purification.

후처리

  1. temperatureto cool to ambient temperature
  2. custompartitioned between diethyl ether and saturated NaHCO3 solution
  3. extractionThe separated aqueous phase was extracted with diethyl ether
  4. washthe combined organic layers were washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-82e318687c99424895ebf2b28a41735b
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06933311B2

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