4-(Piperidin-4-yloxy)benzonitrile → 4-(1-Acetylpiperidin-4-yloxy)benzonitrile

HRID 1949993Notes

Reaction equation

HRID 1949993 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][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.N1CCC(OC2C=CC(C#N)=CC=2)C[CH2:24]1>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][CH:16]=2)[CH2:10][CH2:9]1)(=[O:5])[CH3:24]

Participants

5

Reactant 2

HCID 112411094-(Piperidin-4-yloxy)benzonitrileHCID 23019443tert-Butyl 4-(4-cyanophenoxy)piperidine-1-carboxylate

Product 1

HCID 230870684-(1-Acetylpiperidin-4-yloxy)benzonitrile

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 7918Acetic AnhydrideSolvent

Procedure

Synthesized from 4-(4-cyanophenoxy)piperidine-1-carboxylic acid tert-butyl ester (1.5 g) according to an analogous synthetic method to Example 215 described below, the total amount of 4-(piperidin-4-yloxy)benzonitrile crude product was dissolved in acetic anhydride (20 ml) and pyridine (20 ml), and the solution was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, 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 (1.1 g).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionextracted 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-6dcbe6d32e2642b390d63f5e3906e7b7
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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