Piperidine → HCID 62301426, compound

HRID 1505172Notes

Reaction equation

HRID 1505172 reaction equation
F[C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>>[CH3:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:9]=1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 27784432-Fluoro-4-methylbenzonitrile

Product 1

HCID 62301426HCID 62301426, compoundYield 65%

Conditions

Temperature
80 °C

Procedure

To commercially available 2-fluoro-4-methylbenzonitrile 15b (2.5 g, 18.5 mmol) was added piperidine (4 equiv., 7.3 ml) and the solution was heated at 80° C. overnight. The reaction was evaporated and the residue was dissolved in AcOEt and washed with water and brine. The organic phase was evaporated obtaining 2.3 g of a white solid. Yield=65% 1HNMR (DMSO, 200 MHz) δ 1.62 (6H, m), 2.32 (3H, s), 3.07 (4H, m), 6.87 (1H, dd, J=7.8 Hz, J′=0.8 Hz), 6.95 (1H, s), 7.53 (1H, d, J=7.8 Hz)

Workup

  1. customThe reaction was evaporated
  2. dissolutionthe residue was dissolved in AcOEt
  3. washwashed with water and brine
  4. customThe organic phase was evaporated

Sources & evidence

ORD record
ord-4db6bc18eac34bd194387142a0e745a5
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

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