Trifluoroacetic acid → HCID 18357113, compound

HRID 427467Notes

Reaction equation

HRID 427467 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:21]([C:18]1[CH:19]=[CH:20][C:15]([O:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[N:16][CH:17]=1)#[N:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57027834tert-Butyl 4-(5-cyanopyridin-2-yloxy)piperidine-1-carboxylate

Product 1

HCID 18357113HCID 18357113, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-(t-butyloxycarbonyl),4-(5-cyano,2-pyridinyloxy)piperidine (1.6 g) in dichloromethane (20 mL) was added trifluoroacetic acid (1.2 mL) and the reaction stirred at room temperature for 1 hour. The reaction was quenched by evaporation of trifluoroacetic acid dissolving the residue in water, basifying with sodium hydrogen carbonate and extracting the dichloromethane. The organic layer was then washed with water, brine, dried (MgSO4) and evaporated to yield 4-(5-cyano,2-pyridyloxy)piperidine as a white crystalline solid (337 mg), MS: m/z 279 (MH+).

Workup

  1. customThe reaction was quenched by evaporation of trifluoroacetic acid dissolving the residue in water
  2. extractionextracting the dichloromethane
  3. washThe organic layer was then washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-8d9c80c641f047d8be3eeae9f4cc71c9
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

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