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

HRID 58429Notes

Reaction equation

HRID 58429 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([C:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH:14]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[ClH:28]>C(Cl)Cl.CCOCC>[ClH:28].[F:27][C:2]([F:1])([F:26])[C:3]1[CH:4]=[C:5]([C:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH:14]=2)[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118483354tert-butyl 4-(3,5-bis(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 1184833804-(3,5-Bis(trifluoromethyl)phenyl)-1,2,3,6-tetrahydropyridine hydrochlorideYield 60%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 4-(3,5 bis(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (18, 0.891 g, 2.25 mmol) in CH2Cl2 (13.5 mL) in CH2Cl2 (11 mL) was added HCl (2.0 N solution in Et2O, 11.0 mL) and the mixture 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-(3,5-bis(trifluoromethyl)phenyl)-1,2,3,6-tetrahydropyridine hydrochloride (19) as a white solid (0.452 g, 60%): 1H NMR (300 MHz, DMSO-d6) δ 9.34 (br s, 2H), 8.14-8.09 (m, 2H), 8.08-8.04 (m, 1H), 6.59-6.53 (m, 1H), 3.83-3.74 (m, 2H), 3.38-3.25 (m, 2H), 2.83-2.71 (m, 2H); ESI MS m/z 296 [M+H]+.

Workup

  1. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-1bb865a892e54ee0baef8d1093e976c2
Source dataset
uspto-grants-2016_09
Patent number
US09434727B2

Reaction notes

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