Trifluoroacetic acid → 3-(Piperidin-4-yloxy)pyridine

HRID 1168992Notes

Reaction equation

HRID 1168992 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[NH:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21906079HCID 21906079, compound

Product 1

HCID 121122323-(Piperidin-4-yloxy)pyridine

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

A cold (0-5° C.), stirring solution of 3-(N-(tert-butoxycarbonyl)-4-piperidinyloxy)pyridine (500 mg, 1.796 mmol) in anisole (8 mL) was treated with trifluoroacetic acid (8 mL, 11.84 g, 103.8 mmol). The resulting solution was stirred for 30 min. The volatiles were removed on a rotary evaporator, and the residue was neutralized and basified to pH 9 with solid K2CO3 and water. The mixture was extracted with chloroform (4×20 mL). The combined chloroform extracts were dried (K2CO3), filtered and concentrated. The crude product was purified by column chromatography over silica gel, eluting with chloroform-acetone (9:1, v/v). Selected fractions were collected and concentrated to give 260 mg (81.2%) of an off-white, viscous liquid.

Workup

  1. customThe volatiles were removed on a rotary evaporator
  2. extractionThe mixture was extracted with chloroform (4×20 mL)
  3. dry with materialThe combined chloroform extracts were dried (K2CO3)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography over silica gel
  7. washeluting with chloroform-acetone (9:1
  8. customSelected fractions were collected
  9. concentrationconcentrated
  10. customto give 260 mg (81.2%) of an off-white, viscous liquid

Sources & evidence

ORD record
ord-126f6a7cbdd646989029bda818a8ac70
Source dataset
uspto-grants-2003_09
Patent number
US06627648B1

Reaction notes

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