Hydrochloric Acid → HCID 13755070, compound

HRID 1507184Notes

Reaction equation

HRID 1507184 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 13755070HCID 13755070, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-838b2bafe68d458dbf61f6965cd28ca5
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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