Hydrochloric Acid → HCID 13755070, 화합물

HRID 1507184노트

반응식

HRID 1507184 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)(O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCOCC1>[CH2:1]([N:8]1[CH2:9][C:10]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)=[CH:11][CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 137550691-Benzyl-3-(4-methoxyphenyl)piperidin-3-ol

생성물 1

HCID 13755070HCID 13755070, 화합물수율 35.6%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a solution of 1-benzyl-3-(4-methoxyphenyl)piperidin-3-ol (3.5 g, 11.8 mmol) in dioxane (20 mL) was added concentrated HCl (3.6 mL, 43 mmol) and the reaction mixture was stirred overnight. The solvents were evaporated under reduced pressure and the residue was diluted with sat. bicarbonate solution (200 mL) and extracted with ethyl acetate (200 mL). The organic layer was dried over Na2SO4 and evaporated under reduced pressure to give the crude product which was purified via silica gel chromatography eluting with 30% ethyl acetate in hexane to give 1-benzyl-5-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridine (1.5 g, 4.2 mmol, 35.6% yield). LCMS (Method 107): (ES-API), m/z 280.2 (M+H) RT=2.263 min; 1H NMR (300 MHz, DMSO-d6) δ 7.42-7.32 (m, 4H), 7.29-7.19 (m, 3H), 6.91-6.82 (m, 2H), 6.16-5.97 (m, 1H), 3.73 (s, 3H), 3.65 (d, J=2.6 Hz, 3H), 3.23 (d, J=1.9 Hz, 2H), 2.55 (s, 1H), 2.24 (d, J=3.8 Hz, 2H).

후처리

  1. customThe solvents were evaporated under reduced pressure
  2. additionthe residue was diluted with sat. bicarbonate solution (200 mL)
  3. extractionextracted with ethyl acetate (200 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated under reduced pressure
  6. customto give the crude product which
  7. customwas purified via silica gel chromatography
  8. washeluting with 30% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-838b2bafe68d458dbf61f6965cd28ca5
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221796B2

반응 노트

불러오는 중…