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

HRID 1507189Notes

Reaction equation

HRID 1507189 reaction equation
O[C:2]1([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=2[CH3:23])[CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4][CH2:3]1.[ClH:24]>O1CCOCC1>[ClH:24].[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:2]2[CH2:7][CH2:6][NH:5][CH2:4][CH:3]=2)=[C:16]([CH3:23])[CH:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118207352tert-Butyl 4-hydroxy-4-(4-methoxy-2-methylphenyl)piperidine-1-carboxylate

Product 1

HCID 1182075654-(4-Methoxy-2-methylphenyl)-1,2,3,6-tetrahydropyridine hydrochlorideYield 82%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of tert-butyl 4-hydroxy-4-(4-methoxy-2-methylphenyl)piperidine-1-carboxylate (2.3 g, 7.2 mmol) in 1,4-dioxane (20 mL) was chilled to 0° C. and treated with a solution of HCl in dioxane (4.0 M, 1.8 mL, 7.2 mmol). The reaction mixture was stirred at rt for 12 h, and then the solvents were evaporated to provide a crude compound which was triturated with diethyl ether to provide the desired product as a solid (1.2 g, 82%). LC/MS (Method P) RT=0.63 min. (M+H)+=204.0; 1H NMR (300 MHz, DMSO-d6) δ 9.51-9.09 (m, 2H), 7.00 (d, J=8.3 Hz, 1H), 6.79-6.71 (m, 2H), 5.52 (t, J=1.5 Hz, 1H), 3.73 (s, 3H), 3.67 (br. s., 2H), 3.26 (d, J=4.5 Hz, 2H), 2.45 (d, J=1.9 Hz, 2H), 2.25 (s, 3H)

Workup

  1. customthe solvents were evaporated
  2. customto provide a crude compound which
  3. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-51e146f3d85e4f1d996145c67b94bac7
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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