Trifluoroacetic acid → 3-(3-Piperidinyloxy)pyridine

HRID 2180249Notes

Reaction equation

HRID 2180249 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([O:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:17]1[CH2:18][CH2:19][CH2:20][CH:15]([O:14][C:10]2[CH:9]=[N:8][CH:13]=[CH:12][CH:11]=2)[CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 106602331-Boc-3-(3-pyridinyloxy)piperidine

Product 1

HCID 98153923-(3-Piperidinyloxy)pyridineYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 130 mg of 3-(1-t-butoxycarbonyl-3-piperidinyloxy)-pyridine was added 10 mL of solution containing 5 mL of TFA and 5 mL of CH2Cl2 at ice-bath temperature. The reaction solution was slowly warmed to room temperature and allowed to stir 50 min at room temperature. After 50 min, solvents were removed in vacuo and the crude product was purified by flash chromatography (9:1: 0.05, CHCl3:MeOH:conc. NH4OH) to obtain 83 mg (quantitative yield) of a clear oil: 1H NMR (300 MHz, CD3OD) δ 8.27 (1H, d, J=2.7 Hz), 8.13 (1H, d, J=4.0 Hz), 7.49-7.34 (2H, m), 4.52 (1H, m), 3.20-2.80 (4H, m), 2.05-1.55 (4H, m); Mass spectrum (ESI) m/z 179.6 (M+H+).

Workup

  1. waitAfter 50 min
  2. customsolvents were removed in vacuo
  3. customthe crude product was purified by flash chromatography (9:1: 0.05, CHCl3:MeOH:conc. NH4OH)

Sources & evidence

ORD record
ord-5e3447382f4e4a78a06cdff7847b7d6f
Source dataset
uspto-grants-2005_05
Patent number
US06888001B2

Reaction notes

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