Trifluoroacetic acid → 4-[2-(4-Methanesulfonylphenoxymethyl)pyridin-5-yl]piperidine

HRID 42144

Reaction equation

HRID 42144 reaction equation
[CH3:1][S:2]([C:5]1[CH:31]=[CH:30][C:8]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)=[CH:13][N:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].FC(F)(F)C(O)=O>ClCCl>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[CH:13][N:12]=2)=[CH:30][CH:31]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 44819975Tert-butyl 4-[2-(4-methanesulfonyl-phenoxymethyl)pyridin-5-yl]piperidine-1-carboxylate

Product 1

HCID 670831594-[2-(4-Methanesulfonylphenoxymethyl)pyridin-5-yl]piperidineYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-[2-(4-methanesulfonyl-phenoxymethyl)pyridin-5-yl]piperidine-1-carboxylate (Example 1) (164 mg, 0.367 mmol) in dichloromethane (1.5 mL) was added trifluoroacetic acid (1.5 mL). The mixture was stirred at room temperature overnight and was then concentrated in vacuo. To the residue was added saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound (125 mg, yield 98%).

Workup

  1. concentrationwas then concentrated in vacuo
  2. additionTo the residue was added saturated aqueous sodium hydrogen carbonate solution
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7bbf671fa1444f3896c4b029c89881db
Source dataset
uspto-grants-2013_09
Patent number
US08536176B2

Linked notes

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