Piperidine → HCID 58873258, compound

HRID 1505158Notes

Reaction equation

HRID 1505158 reaction equation
Cl[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>>[F:11][C:10]([F:13])([F:12])[C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:9]=1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 27364762-Chloro-4-(trifluoromethyl)benzonitrile

Product 1

HCID 58873258HCID 58873258, compoundYield 56%

Conditions

Temperature
80 °C

Procedure

To commercially available 2-chloro-4-trifluoromethylbenzonitrile 13 (1 ml, 7.2 mmol) was added piperidine (4 equiv., 2.8 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 1 g of a yellow oil. Yield=56% 1HNMR (DMSO, 200 MHz) δ 1.60 (6H, m), 3.20 (4H, m), 7.34 (2H, m), 7.89 (1H, dd, J=8.6 Hz, J′=0.4 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-fce64cade1ac4be7b89560c563177a18
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

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