1-Benzyl-4-piperidone → 1-Benzyl-4-(3-bromo-2-ethylphenyl)piperidin-4-ol

HRID 1942682노트

반응식

HRID 1942682 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[CH2:9][CH3:10].[Li]CCCC.[CH2:16]([N:23]1[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[NH4+].[Cl-]>C1COCC1>[CH2:16]([N:23]1[CH2:28][CH2:27][C:26]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=2[CH2:9][CH3:10])([OH:29])[CH2:25][CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

참가 물질

6

반응물 4

HCID 192201-Benzyl-4-piperidoneHCID 25517Ammonium ChlorideHCID 148478061,3-Dibromo-2-ethylbenzeneHCID 178418339Butyllithium

생성물 1

HCID 584940321-Benzyl-4-(3-bromo-2-ethylphenyl)piperidin-4-ol수율 71.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 1,3-dibromo-2-ethyl-benzene (30 g, 113.65 mmol) in THF (150 mL) was added 45.5 mL of BuLi (2.5M in hexane, 113.65 mmol) under nitrogen. The mixture was stirred for 4 hr at −78° C. Then N-benzyl-4-piperidone (21.51 g, 113.65 mmol) was added to the above mixture and stirred overnight, The mixture was poured into sat. aqueous NH4Cl solution and extracted with DCM. The organic layer was separated, dried over Na2SO4, and concentrated under reduced pressure give the crude 1-benzyl-4-(3-bromo-2-ethyl-phenyl)-piperidin-4-ol (D116) (30.4 g). MS (ES): C20H24BrNO requires 373. found 374 (M+H+).

후처리

  1. stirringstirred overnight
  2. extractionextracted with DCM
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-33ce6ab8864c49d7964cceb67f7b8565
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389508B2

반응 노트

불러오는 중…