2-(4'Fluorophenyl) aminocyclohex-1-ene-1-carbonitrile → 9-Amino-7-fluoro-1, 2, 3, 4-tetrahydro-acridine

HRID 366401Notes

Reaction equation

HRID 366401 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[C:15]#[N:16])=[CH:4][CH:3]=1>[Ti](Cl)(Cl)(Cl)Cl.[OH-].[Na+]>[NH2:16][C:15]1[C:6]2[C:5]([N:8]=[C:9]3[C:10]=1[CH2:11][CH2:12][CH2:13][CH2:14]3)=[CH:4][CH:3]=[C:2]([F:1])[CH:7]=2

Participants

4

Reactant 1

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

Product 1

HCID 508520829-Amino-7-fluoro-1, 2, 3, 4-tetrahydro-acridine

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
140 °C

Procedure

Under nitrogen, titanium tetrachloride (0.9 ml, 8.2 mmol) was added to the above enamine (Example 33) (1.5 g, 7.5 mmol) and the stirred mixture was heated at 140° C. for 1 hour. After cooling, 10M-sodium hydroxide solution (20 ml) was added and the mixture heated under reflux for 1 hour. After being allowed to cool, this mixture was filtered and the solids washed with dichloromethane. Any organics in the filtrate were also extracted into dichloromethane. All extracts were combined, dried (Na2SO4), filtered and the solvent evaporated. Kugelrohr distillation (175° C., 0.05 mmHg) gave the product as a pale yellow powder.

Workup

  1. temperatureAfter cooling
  2. temperaturethe mixture heated
  3. temperatureunder reflux for 1 hour
  4. temperatureto cool
  5. filtrationthis mixture was filtered
  6. washthe solids washed with dichloromethane
  7. extractionAny organics in the filtrate were also extracted into dichloromethane
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customthe solvent evaporated
  11. distillationKugelrohr distillation (175° C., 0.05 mmHg)

Sources & evidence

ORD record
ord-ea0867e2c5ed44b694b720f60282016c
Source dataset
uspto-grants-2000_10
Patent number
US06130228

Reaction notes

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