Acetyl chloride → 4-(Piperidin-4-yloxy)benzonitrile hydrochloride

HRID 459925

Reaction equation

HRID 459925 reaction equation
C([Cl:4])(=O)C.C(OC([N:12]1[CH2:17][CH2:16][CH:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)=O)(C)(C)C>CO>[ClH:4].[NH:12]1[CH2:13][CH2:14][CH:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=2)[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 23019443tert-Butyl 4-(4-cyanophenoxy)piperidine-1-carboxylate

Product 1

HCID 178322734-(Piperidin-4-yloxy)benzonitrile hydrochlorideYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

Add dropwise acetyl chloride (2.5 mL) to methanol (5.0 mL) at 0° C. Stir the resulting solution at 0° C. for 90 min. Then add a solution of 4-(4-cyano-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (284 mg, 0.94 mmol) in methanol. Stir the resulting mixture for 3 h. Evaporate the solvent and triturate with diethyl ether to provide the title compound (216 mg, 96%).

Workup

  1. stirringStir the resulting mixture for 3 h
  2. customEvaporate the solvent
  3. customtriturate with diethyl ether

Sources & evidence

ORD record
ord-494f68581f2d484bbc465e010094f0fe
Source dataset
uspto-grants-2007_03
Patent number
US07196100B2

Linked notes

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