Hydrochloric Acid → 4-(3-Fluoro-4-methoxyphenyl)-1,2,3,6-tetrahydropyridine hydrochloride

HRID 1507205Notes

Reaction equation

HRID 1507205 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2(O)[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[ClH:24]>O1CCOCC1>[ClH:24].[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118207351tert-Butyl 4-(3-fluoro-4-methoxyphenyl)-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 668652484-(3-Fluoro-4-methoxyphenyl)-1,2,3,6-tetrahydropyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of tert-butyl 4-(3-fluoro-4-methoxyphenyl)-4-hydroxypiperidine-1-carboxylate (6.5 g, 20 mmol) in 1,4-dioxane (100 mL) at 0° C. was added 50 mL of 1M HCl (dioxane solution) and the mixture was allowed to warm to rt and stirred for 12 h. The solvent was then removed under reduced pressure. The residue was triturated with ethyl acetate to obtain 4.5 g crude 4-(3-fluoro-4-methoxyphenyl)-1,2,3,6-tetrahydropyridine hydrochloride as a solid which was was isolated by filtration and used without further purification. LCMS (Method P) RT 0.57 min, m/z 208 (M+H+); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.37-2.61 (m, 2H), 3.12-3.38 (m, 3H) 3.80-3.94 (m, 3H) 3.95-4.12 (m, 2H) 7.10-7.29 (m, 1H) 7.33-7.44 (m, 1H) 7.51 (dd, J=13.05, 2.51 Hz, 1H) 9.27-9.63 (m, 2H).

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-96ed16584baa4eb6b8dcccbb40760b15
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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