4-Fluorobenzonitrile → 4-(4-Methyl-piperidin-1-yl)-benzonitrile

HRID 1354776Notes

Reaction equation

HRID 1354776 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH3:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>C(OCC)(=O)C>[CH3:10][CH:11]1[CH2:16][CH2:15][N:14]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 145174-FluorobenzonitrileHCID 693814-Methylpiperidine

Product 1

HCID 31520804-(4-Methyl-piperidin-1-yl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Fluorobenzonitrile (1.21 g) was heated with 4-methylpiperidine (1.00 g) at 180° C. for 1 hour. The mixture was then taken up in ethyl acetate, washed with water, 2N sodium hydroxide solution and saturated sodium bicarbonate solution, dried over sodium sulfate, concentrated and crystallized from n-pentane. This resulted in the product with the molecular weight of 200.29 (C13H16N2); MS(ESI): 201 (M+H+).

Workup

  1. washwashed with water, 2N sodium hydroxide solution and saturated sodium bicarbonate solution
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customcrystallized from n-pentane
  5. customThis resulted in the product with the molecular weight of 200.29 (C13H16N2)

Sources & evidence

ORD record
ord-d4982c217d27448886b5e99d7176c7a3
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

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