Potassium Hydroxide → 8-fluoro-11-(4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

HRID 569214Notes

Reaction equation

HRID 569214 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:21][CH2:20][N:19](C(OCC)=O)[CH2:18][CH2:17]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:27]=1.[OH-].[K+]>C(O)C.O.[Cl-].[Na+].O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:27]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 139205968-Fluoro-11(1-ethoxycarbonyl-4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

Product 1

HCID 139205978-fluoro-11-(4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridineYield 95.9%

Reagents, catalysts & solvents 2

HCID 19096565Water ethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 8-fluoro-6,11-dihydro-11-(1-ethoxycarbonyl-4-piperidylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine (3.6 g, 0.0098 mole) and potassium hydroxide (4.5 g, 0.094 mole) in 50 mL of ethanol:water (1:1) is heated at reflux for 66 hours. The reaction mixture is diluted with brine and the product is extracted into ethyl acetate. The solution is concentrated to a residual solid which is washed with acetone/ethyl acetate to yield 2.76 g (0.0094 mole) of 8-fluoro-11-(4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine.

Workup

  1. temperatureat reflux for 66 hours
  2. extractionthe product is extracted into ethyl acetate
  3. concentrationThe solution is concentrated to a residual solid which
  4. washis washed with acetone/ethyl acetate

Sources & evidence

ORD record
ord-d4e671b12db0456284d83f01e66c8011
Source dataset
uspto-grants-1988_03
Patent number
US04731447

Reaction notes

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