Trifluoroacetic acid → 2-(3-Methyl-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine

HRID 1666455Notes

Reaction equation

HRID 1666455 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][N:24]=2)[CH:21]=1)[CH:5]=[C:6]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:21]=[C:20]([CH:19]=[C:4]([CH:5]=[C:6]2[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH:3]=1)[O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:25][N:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66876309tert-Butyl 4-(3-methyl-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

Product 1

HCID 668761222-(3-Methyl-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridineYield 116.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(3-methyl-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (0.50 g, 0.0011 mol) in CH2Cl2 (5 mL) cooled to 0° C. under a N2 atmosphere was added TFA (0.85 mL, 0.011 mol) slowly. The resulting mixture was stirred for 2 h at RT. The solution was concentrated under reduced pressure to give the title compound (445 mg).

Workup

  1. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9295a53cc4b142abaccb186ce77e5890
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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