Hydrochloric Acid → HCID 13755070、化合物

HRID 1507184ノート

反応式

HRID 1507184 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 13755070HCID 13755070、化合物収率 35.6%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-838b2bafe68d458dbf61f6965cd28ca5
出典データセット
uspto-grants-2015_12
特許番号
US09221796B2

反応ノート

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