Hydrochloric Acid → 5-(4-Fluorophenyl)-2-(piperidin-4-yloxy)pyridine

HRID 393717Notes

Reaction equation

HRID 393717 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]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>CO.C(OCC)C>[F:27][C:24]1[CH:23]=[CH:22][C:21]([C:18]2[CH:19]=[CH:20][C:15]([O:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[N:16][CH:17]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 698966684-[5-(4-Fluorophenyl)pyridin-2-yloxy]piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 226467305-(4-Fluorophenyl)-2-(piperidin-4-yloxy)pyridineYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

4-[5-(4-fluorophenyl)pyridin-2-yloxy]piperidine-1-carboxylic acid tert-butyl ester (0.88 g) was dissolved in methanol (20 ml) and treated dropwise with a 1.0 M solution of HCl in diethyl ether (24 ml). After stirring for 24 h, the resultant mixture was evaporated. The residue was dissolved in 2% citric acid (30 ml) and washed with diethyl ether (2×15 ml). The aqueous phase was then basified with sodium hydroxide to pH 13 and extracted with ethyl acetate (3×30 ml). The combined ethyl acetate extracts were then washed with water (3×10 ml), saturated brine (10 ml), dried (Na2SO4) and evaporated to furnish the title compound as a white solid (0.52 g, 81%)

Workup

  1. customthe resultant mixture was evaporated
  2. dissolutionThe residue was dissolved in 2% citric acid (30 ml)
  3. washwashed with diethyl ether (2×15 ml)
  4. extractionextracted with ethyl acetate (3×30 ml)
  5. washThe combined ethyl acetate extracts were then washed with water (3×10 ml), saturated brine (10 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-e246a35f6c184966bfee8e6e336e920b
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Reaction notes

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