Trifluoroacetic acid → 2-(3-(1-(Piperidin-4-ylidene)ethyl)phenoxy)-5-(trifluoromethyl)pyridine trifluoroacetate

HRID 1666479Notes

Reaction equation

HRID 1666479 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:11]=[C:12]([C:16](=[C:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)[CH3:17])[CH:13]=[CH:14][CH:15]=2)=[N:7][CH:8]=1.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>C(Cl)Cl>[F:36][C:35]([F:38])([F:37])[C:33]([OH:39])=[O:34].[NH:21]1[CH2:22][CH2:23][C:18](=[C:16]([C:12]2[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=2)[O:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:32])([F:1])[F:31])=[CH:8][N:7]=2)[CH3:17])[CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66876390tert-Butyl 4-(1-(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)ethylidene)piperidine-1-carboxylate

Product 1

HCID 866239122-(3-(1-(Piperidin-4-ylidene)ethyl)phenoxy)-5-(trifluoromethyl)pyridine trifluoroacetateYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 4-(1-(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)ethylidene)piperidine-1-carboxylate (265 mg, 0.591 mmol) in CH2Cl2 (8 mL) was added TFA (2 mL). The reaction was stirred at RT overnight and concentrated to give an oil. This was redissolved in CH2Cl2 and concentrated to give the title compound as an oil (275 mg, 97% yield).

Workup

  1. concentrationconcentrated
  2. customto give an oil
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1d909165719d4395b59f88c576a1b974
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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