4-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridine hydrochloride synthesis

6synthesis methods

Product Name:4-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridine hydrochloride
CAS Number:143017-63-4
Molecular formula:C12H16ClNO
Molecular Weight:225.72

1-BOC-4-(4-METHOXYPHENYL)-4-HYDROXYPIPERIDINE

302924-67-0
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4-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridine hydrochloride

143017-63-4
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Yield:143017-63-4 93%

Reaction Conditions:

with hydrogenchloride in 1,4-dioxane at 20; for 3 h;

Steps:

O Intermediate O. 4-(4-Methoxyphenyl)-1,2,3,6-tetrahydropyridine hydrochloride

Intermediate O. 4-(4-Methoxyphenyl)-1,2,3,6-tetrahydropyridine hydrochloride [0054] tert-butyl 4-hydroxy-4-(4-methoxyphenyl)piperidine-1-carboxylate (700 mg, 2.27 mmol, intermediate N) and HCl in dioxane (4.0 ml, 16 mmol) was stirred at rt for 3 h. The crude mass was concentrated under vacuum and the solid residue was washed with 3×10 ml of DCM to remove non-polar impurities. The desired salt was collected as a fine solid (480 mg, 93%). LCMS (ES-API) m/z 190.2 (M+H)⁺; ¹H NMR (400 MHz, DMSO-d₆) δ 7.37 (d, J=9.0 Hz, 2H), 6.98 (d, J=9.0 Hz, 2H), 6.08-5.98 (m, 1H), 5.11 (s, 1H), 3.97 (br. s., 1H), 3.52 (s, 1H), 3.32 (s, 3H), 2.47-2.37 (m, 1H).

References:

US2015/191496,2015,A1 Location in patent:Paragraph 0054-0055

104-92-7 Synthesis