HCID 23087388, compound → HCID 23087488, compound

HRID 1950000Notes

Reaction equation

HRID 1950000 reaction equation
C([O:5][C:6]([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][C:16]=2[F:23])[CH2:10][CH2:9]1)=O)(C)(C)C.F[C:25]1C=C(C=CC=1OC1CCNCC1)C#N>C(OC(=O)C)(=O)C.N1C=CC=CC=1>[C:6]([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][C:16]=2[F:23])[CH2:10][CH2:9]1)(=[O:5])[CH3:25]

Participants

5

Reactant 2

HCID 23087388HCID 23087388, compoundHCID 57933849HCID 57933849, compound

Product 1

HCID 23087488HCID 23087488, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 7918Acetic AnhydrideSolvent

Procedure

Synthesized from 4-(4-cyano-2-fluorophenoxy)piperidine-1-carboxylic acid tert-butyl ester (2.8 g) according to an analogous synthetic method to Example 215 described below, the total amount of 3-fluoro-4-(piperidin-4-yloxy)benzonitrile crude product was dissolved in acetic anhydride (30 ml) and pyridine (30 ml), and the solution was stirred overnight at room temperature. The solvent was evaporated in vacuo, the solution was extracted with ethyl acetate, then sequentially washed with a saturated aqueous solution of sodium bicarbonate, water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (2.2 g).

Workup

  1. customThe solvent was evaporated in vacuo
  2. extractionthe solution was extracted with ethyl acetate
  3. washsequentially washed with a saturated aqueous solution of sodium bicarbonate, water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-3fd2e7cc49584718aa8ea53fff54c20a
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

Loading…