4-Fluoroaniline → 2-(4'Fluorophenyl) aminocyclohex-1-ene-1-carbonitrile

HRID 366400Notes

Reaction equation

HRID 366400 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.O=[C:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[C:16]#[N:17].[Cl-].[Ca+2].[Cl-]>>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:16]#[N:17])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 97314-FluoroanilineHCID 2202972-OxocyclohexanecarbonitrileHCID 5284359Calcium Chloride

Product 1

HCID 702554742-(4'Fluorophenyl) aminocyclohex-1-ene-1-carbonitrile

Procedure

4-Fluoro-aniline (1.11 g, 10.0 mmol), cyano-ketone (Example 32) (1.25 g, 10.2 mmol), calcium chloride (1.5 g, 13.5 mmol) and T.H.F. (20 ml) were heated under reflux for 17 hours. After cooling, the mixture was filtered and the solvent evaporated. Kugelrohr distillation (135° C., 0.08 mmHg) gave the product as a pale yellow powder.

Workup

  1. temperature(20 ml) were heated
  2. temperatureunder reflux for 17 hours
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. customthe solvent evaporated
  6. distillationKugelrohr distillation (135° C., 0.08 mmHg)

Sources & evidence

ORD record
ord-686a9c224c1149408ed9747acb345109
Source dataset
uspto-grants-2000_10
Patent number
US06130228

Reaction notes

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