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

HRID 542757Notes

Reaction equation

HRID 542757 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 95.7%

Reagents, catalysts & solvents 2

HCID 19096565Water ethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

8-Fluoro-11-(1-ethoxycarbonyl-4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine (3.6 g, 9.8 mmol.) was refluxed with KOH (4.5 g) in 50 mL of ethanol/water (1:1) for 66 hours under an argon atmosphere. The reaction mixture was poured into a brine solution and extracted twice with ethyl acetate. The extracts were combined and then dried over Na2SO4 and filtered. Solvent was removed to give 2.76 grams (yield=95%) of the title compound, m.p.=133.5°-134.5° C.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customSolvent was removed

Sources & evidence

ORD record
ord-304ceaeaba1f4aec9ead2888124616f5
Source dataset
uspto-grants-1987_04
Patent number
US04659716

Reaction notes

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