Diethyl Ether → 1-(4-Bromo-2-(methoxymethyl)phenyl)-2-methylpiperidine

HRID 219872

반응식

HRID 219872 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[CH3:16])=[C:6]([CH2:8][OH:9])[CH:7]=1.[CH2:17](N(C(C)C)C(C)C)C.CS(Cl)(=O)=O.CCOCC>C(Cl)Cl.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[CH3:16])=[C:6]([CH2:8][O:9][CH3:17])[CH:7]=1

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58554197(5-Bromo-2-(2-methylpiperidin-1-YL)phenyl)methanol

생성물 1

HCID 585541231-(4-Bromo-2-(methoxymethyl)phenyl)-2-methylpiperidine수율 156.4%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

반응 조건

온도
50 °C

실험 절차

To a solution of solution of [5-bromo-2-(2-methylpiperidin-1-yl)phenyl]methanol (7.9 g; 27.8 mmol) and n-ethyldiisopropylamine (10.40 mL; 61.15 mmol) in anhydrous DCM (150 mL) cooled to 0° C., was added methanesulfonyl chloride (2.36 mL; 30.57 mmol). The reaction mixture was diluted with MeOH (150 mL) and heated to 50° C. for 3 h after which time solvents were removed under vacuum to give a brown oil. Residue was taken up with Et2O (450 mL), washed with water (150 mL, pH 8 adjusted with aqueous NaOH), saturated aqueous solution of NH4Cl (2×150 mL) and brine (150 mL). The combined organic layers were dried over MgSO4, filtered and the solvent was removed under reduced pressure to give the title compound as a brown yellow oil (12.97 g, 92%). LC/MS (Method B): 298.1 (M+H)+.

후처리

  1. customwere removed under vacuum
  2. customto give a brown oil
  3. washwashed with water (150 mL, pH 8 adjusted with aqueous NaOH), saturated aqueous solution of NH4Cl (2×150 mL) and brine (150 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-e44ed2c331294eb89cf18ac3e1d755e3
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202865B2

연결된 노트

불러오는 중…