Piperidine → 4-piperidin-1-ylbenzonitrile

HRID 1505167Notes

Reaction equation

HRID 1505167 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>>[N:10]1([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 121634-Chlorobenzonitrile

Product 1

HCID 7667714-piperidin-1-ylbenzonitrileYield 89%

Conditions

Temperature
100 °C

Procedure

To commercially available 4-chlorobenzonitrile 17 (1 g, 7.26 mmol) 3 ml of piperidine were added and the reaction was heated at 100° C. for 72 hours in closed vessel. The reaction was evaporated and the residue was dissolved in AcOEt and washed with water and brine. The purification of the crude residue by chromatographic column using AcOEt 1/Petroleum ether 9 as eluant gave 1.2 g of a pale yellow oil. Yield=89% 1HNMR (DMSO, 200 MHz) δ 1.57 (6H, m), 3.34 (4H, m), 6.98 (2H, d, J=9 Hz), 7.53 (2H, d, J=9 Hz)

Workup

  1. customThe reaction was evaporated
  2. dissolutionthe residue was dissolved in AcOEt
  3. washwashed with water and brine
  4. customThe purification of the crude residue by chromatographic column

Sources & evidence

ORD record
ord-1e0c9dab523544ef9e18f4b8b5dc5e5c
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

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