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

HRID 716087Notes

Reaction equation

HRID 716087 reaction equation
O[C:2]1([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4][CH2:3]1.[ClH:23].O1CCOCC1>>[ClH:23].[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([C:2]2[CH2:7][CH2:6][NH:5][CH2:4][CH:3]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 49760247Tert-butyl 4-hydroxy-4-(4-methoxyphenyl)piperidine-1-carboxylate2×

Product 1

HCID 214736704-(4-Methoxyphenyl)-1,2,3,6-tetrahydropyridine hydrochloride

Procedure

A mixture of 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).

Workup

  1. concentrationThe crude mass was concentrated under vacuum
  2. washthe solid residue was washed with 3×10 ml of DCM
  3. customto remove non-polar impurities
  4. customThe desired salt was collected as a fine solid (480 mg, 93%)

Sources & evidence

ORD record
ord-9d4615c76b9c41e3b61886122a0fe47c
Source dataset
uspto-grants-2015_11
Patent number
US09187506B2

Reaction notes

Loading…