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

HRID 1507191Notes

Reaction equation

HRID 1507191 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 hydrochlorideYield 82%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of tert-butyl 4-(3-fluoro-4-methoxyphenyl)-4-hydroxypiperidine-1-carboxylate (0.5 g, 1.5 mmol) in 1,4-dioxane (20 mL) was chilled to 0° C. and treated with a solution of HCl in 1,4 dioxane (4.0 M, 10 mL, 40 mmol). The reaction mixture was stirred at rt for 12 h, and then the solvents were removed 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 109) RT=1.798 min. (M+H)+=207.8; 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 removed
  2. customto provide a crude compound which
  3. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-4da86da7be8047ff93d696410ef22824
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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