Trifluoroacetic acid → (4-(Aminomethyl)pyridin-2-yl)(4-(4-chlorophenoxy)piperidin-1-yl)methanone

HRID 2170855Notes

Reaction equation

HRID 2170855 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([O:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:20]=[C:19]([CH2:21][NH:22]C(=O)OC(C)(C)C)[CH:18]=[CH:17][N:16]=3)=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:22][CH2:21][C:19]1[CH:18]=[CH:17][N:16]=[C:15]([C:13]([N:10]2[CH2:11][CH2:12][CH:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:31][CH:30]=3)[CH2:8][CH2:9]2)=[O:14])[CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68204542HCID 68204542, compound

Product 1

HCID 67168014(4-(Aminomethyl)pyridin-2-yl)(4-(4-chlorophenoxy)piperidin-1-yl)methanoneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl ((2-(4-(4-chlorophenoxy)piperidine-1-carbonyl)pyridin-4-yl)methyl)carbamate (165 mg, 0.37 mmol, Step-1), trifluoroacetic acid (2 mL), and dichloromethane (2 mL) was stirred at room temperature for 1 hour. After removal of the solvent, the residue was purified by a strong cation exchange cartridge (BondElute(registered trademark) SCX) to give 128 mg (>99%) of the title compound as colorless syrup. 25 mg of this material was further purified by preparative LC-MS to give 16.9 mg (68% yield) of the title compound.

Workup

  1. customAfter removal of the solvent
  2. customthe residue was purified by a strong cation exchange cartridge (BondElute(registered trademark) SCX)

Sources & evidence

ORD record
ord-bc77297318344b798fac17fb24a90332
Source dataset
uspto-grants-2015_06
Patent number
US09051296B2

Reaction notes

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