Trifluoroacetic acid → 5-Cyclopropyl-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridine trifluoroacetate

HRID 1666384Notes

Reaction equation

HRID 1666384 reaction equation
[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([O:10][C:11]3[CH:12]=[C:13]([CH:28]=[CH:29][CH:30]=3)[CH:14]=[C:15]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34]>C(Cl)Cl>[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34].[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([O:10][C:11]3[CH:30]=[CH:29][CH:28]=[C:13]([CH:14]=[C:15]4[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]4)[CH:12]=3)=[N:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66876584tert-Butyl 4-(3-(5-cyclopropylpyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

Product 1

HCID 668761235-Cyclopropyl-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridine trifluoroacetateYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 4-(3-(5-cyclopropylpyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (350 mg, 0.861 mmol) in CH2Cl2 (10 mL) was added trifluoroacetic acid (2 mL, 25.8 mmol). The reaction was stirred at RT overnight. The reaction was concentrated to give an oil. CH2Cl2 was added and the mixture was concentrated again to give the title compound as an oil (253 mg, 70% yield).

Workup

  1. concentrationThe reaction was concentrated
  2. customto give an oil
  3. concentrationthe mixture was concentrated again

Sources & evidence

ORD record
ord-7954c756f68645169b54624cd006d633
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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