Thionyl Chloride → 1-Benzyl-2-(chloromethyl)piperidine

HRID 538662노트

반응식

HRID 538662 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:18])=O>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][Cl:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 2735486(1-Benzylpiperidin-2-yl)methanol

생성물 1

HCID 150154541-Benzyl-2-(chloromethyl)piperidine

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a stirred solution of compound 13 (3.6 g, 15.00 mmol) in chloroform (50 mL) was added thionyl chloride (1.34 mL) at 0° C. The reaction mixture was heated at reflux for 2 hours and then concentrated. The residue was dissolved in EtOAc and washed with saturated sodium bicarbonate solution, water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified by chromatography on 230-400 mesh silica gel eluting with 10% EtOAc-hexane to provide compound 14 as an oil.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 hours
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with saturated sodium bicarbonate solution, water and brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by chromatography on 230-400 mesh silica gel eluting with 10% EtOAc-hexane

출처 및 근거

ORD 기록
ord-411c250c3a24456caa4a517d6cf6d979
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865741B2

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