Benzene, 1-bromo-2-(trifluoromethyl)- → 1-Benzyl-4-[2-(trifluoromethyl)phenyl]piperidin-4-ol

HRID 1592872노트

반응식

HRID 1592872 반응식
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([F:12])([F:11])[F:10].[CH2:13]([N:20]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[NH4+]>C1COCC1>[CH2:13]([N:20]1[CH2:25][CH2:24][C:23]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:9]([F:12])([F:11])[F:10])([OH:26])[CH2:22][CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

참가 물질

6

반응물 4

HCID 9806Benzene, 1-bromo-2-(trifluoromethyl)-HCID 192201-Benzyl-4-piperidoneHCID 25517Ammonium ChlorideHCID 5462224Magnesium

생성물 1

HCID 232942051-Benzyl-4-[2-(trifluoromethyl)phenyl]piperidin-4-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

A mixture of 1.52 g of magnesium in 25 ml of THF is admixed dropwise over 20 minutes with a solution of 14.25 g of 1-bromo-2-(trifluoromethyl)benzene in 15 ml of THF and the mixture is heated at reflux for 30 minutes. After it has cooled on an ice bath, it is admixed slowly with a solution of 10 g of 1-benzyl-4-piperidinone in 30 ml of THF and left with stirring at AT for 3 hours. The reaction mixture is poured into saturated aqueous ammonium chloride solution and extracted with AcOEt, the combined organic phases are washed with water and dried over Na2SO4 and the solvents are evaporated under vacuum. The residue is chromatographed on silica gel, eluting with a DCM/AcOEt (70/30; v/v) mixture. This gives 4.5 g of the expected product.

후처리

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 30 minutes
  3. temperatureAfter it has cooled on an ice bath
  4. waitleft
  5. extractionextracted with AcOEt
  6. washthe combined organic phases are washed with water
  7. dry with materialdried over Na2SO4
  8. customthe solvents are evaporated under vacuum
  9. customThe residue is chromatographed on silica gel
  10. washeluting with a DCM/AcOEt (70/30; v/v) mixture

출처 및 근거

ORD 기록
ord-bb3b6b9c4c4d466d840d8feaac8154ca
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07294628B2

반응 노트

불러오는 중…