4-Fluorobenzonitrile → N-(4-Cyanophenyl)-4-piperidone propylene ketal

HRID 842784Notes

Reaction equation

HRID 842784 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH2:10]1[O:20][C:14]2([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[O:13][CH:11]1[CH3:12]>ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>[CH2:10]1[O:20][C:14]2([CH2:19][CH2:18][N:17]([C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=3)[CH2:16][CH2:15]2)[O:13][CH:11]1[CH3:12]

Participants

5

Reactant 2

HCID 145174-FluorobenzonitrileHCID 129541174-Piperidone propylene ketal

Product 1

HCID 57228643N-(4-Cyanophenyl)-4-piperidone propylene ketal

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 4-fluorobenzonitrile (1.22 g, 10.0 mmol) and 4-piperidone propylene ketal (2.02 g, 12.85 mmol) was stirred at room temperature overnight. The resulting mixture was diluted with dichloromethane and sodium carbonate solution and the aqueous layer was extracted with two additional portions of dichloromethane. The combined organic extracts were washed with brine and dried over Na2SO4. The solvent was removed in vacuo. PCTLC (SiO2, 6 mm, 10% EtOH-90% CHCl3) afforded the title compound (34).

Workup

  1. extractionthe aqueous layer was extracted with two additional portions of dichloromethane
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e3f82736699c42a688c96bdd22b6876d
Source dataset
uspto-grants-2002_04
Patent number
US06376503B1

Reaction notes

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