Hydrochloric Acid → 4-(5-Fluoro-2-(trifluoromethyl)phenyl)-1,2,3,6-tetrahydropyridine hydrochloride

HRID 58420Notes

Reaction equation

HRID 58420 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:21]([F:24])([F:23])[F:22])=[C:6]([C:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH:9]=2)[CH:7]=1.[ClH:25]>C(Cl)Cl.CCOCC>[ClH:25].[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:21]([F:24])([F:22])[F:23])=[C:6]([C:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH:9]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118483476tert-butyl 4-(5-fluoro-2-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 1184835214-(5-Fluoro-2-(trifluoromethyl)phenyl)-1,2,3,6-tetrahydropyridine hydrochlorideYield 88%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 4-(5-fluoro-2-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (9, 0.542 g, 1.58 mmol) and HCl (2 N solution in Et2O, 10 mL) in CH2Cl2 (20 mL) stirred at ambient temperature for 18 h. The reaction mixture was diluted with Et2O (30 mL), and the resulting precipitate was collected by filtration to provide 4-(5-fluoro-2-(trifluoromethyl)phenyl)-1,2,3,6-tetrahydropyridine hydrochloride (10) as a white solid (0.393 g, 88%): 1H NMR (300 MHz, DMSO-d6) δ 9.26-9.00 (m, 2H), 7.84 (dd, J=8.7, 5.4 Hz, 1H), 7.46-7.36 (m, 1H), 7.24 (dd, J=9.3, 2.4 Hz, 1H), 5.67 (br s, 1H), 3.76-3.64 (m, 2H), 3.27 (t, J=5.1 Hz, 2H), 2.70-2.40 (m, 2H).

Workup

  1. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-3e2ae060fba5494b8baf44b1993d4139
Source dataset
uspto-grants-2016_09
Patent number
US09434727B2

Reaction notes

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