Hydrochloric Acid → 5-(3-(Piperidin-4-ylidenemethyl)phenoxy)-2-(trifluoromethyl)pyridine hydrochloride

HRID 1666434Notes

Reaction equation

HRID 1666434 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[N:8]=[CH:7][C:6]([O:9][C:10]2[CH:11]=[C:12]([CH:27]=[CH:28][CH:29]=2)[CH:13]=[C:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)=[CH:5][CH:4]=1.[ClH:32]>ClCCl>[ClH:32].[NH:17]1[CH2:18][CH2:19][C:14](=[CH:13][C:12]2[CH:11]=[C:10]([CH:29]=[CH:28][CH:27]=2)[O:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:31])([F:1])[F:30])=[N:8][CH:7]=2)[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 668757901,1-Dimethylethyl 4-[[3-[[6-(trifluoromethyl)-3-pyridinyl]oxy]phenyl]methylene]-1-piperidinecarboxylate

Product 1

HCID 668761645-(3-(Piperidin-4-ylidenemethyl)phenoxy)-2-(trifluoromethyl)pyridine hydrochlorideYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-(3-(6-(trifluoromethyl)pyridin-3-yloxy)benzylidene)piperidine-1-carboxylate (0.140 g) in dichloromethane (5 mL, 0.06 M) was treated with hydrogen chloride gas for 2 min. The reaction was allowed to stir for 2 h and then was concentrated to give the title compound as a white foam (0.100 g, 84% yield) which was used without purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.50 (2H, t, J=5.8 Hz), 2.59 (2H, t, J=5.8 Hz), 3.04 (2H, t, J=6.0 Hz), 3.10 (2H, t, J=6.0 Hz), 6.44 (1H, s), 7.01-7.09 (2H, m), 7.13 (1H, d, J=7.8 Hz), 7.43 (1H, t, J=7.8 Hz), 7.52 (1H, dd, J=8.6, 2.7 Hz), 7.88 (1H, d, J=8.6 Hz), 8.52 (1H, d, J=2.7 Hz), 8.98 (2H, br. s.).

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-824129e92ecb4ca29c4cc69fbca2adfa
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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