Sodium Hydroxide → 8-Chloro-11-(4-piperidinylidene)-11H-benzo[5,6]cyclohepta[1,2-b]pyridine

HRID 1534583Notes

Reaction equation

HRID 1534583 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:21][CH2:20][N:19](C(OCC(Cl)(Cl)Cl)=O)[CH2:18][CH2:17]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH:8]=[CH:7][C:6]=2[CH:30]=1.[OH-].[Na+]>C(O)(=O)C.[Zn]>[Cl: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[CH:8]=[CH:7][C:6]=2[CH:30]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22914784HCID 22914784, compound

Product 1

HCID 157805098-Chloro-11-(4-piperidinylidene)-11H-benzo[5,6]cyclohepta[1,2-b]pyridineYield 53%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

A mixture of 210 mg (0.434 mmole) of 8-chloro-11-[1-(2,2,2-trichloroethoxycarbonyl)-4-piperidylidene)-11H-benzo-[5,6]cyclohepta[1,2-b]pyridine and 526 mg (8.05 mmole) of zinc dust in 0.4 mL of acetic acid was heated at 60°-70° C. After 2 hr. 20 min. another 547 mg (8.37 mmole) of zinc dust was added. After another 30 min. the mixture was basified with 10% aqueous NaOH and extracted four times with CH2Cl2. The combined organic portions were washed once with water, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified via flash chromatography [5→6% MeOH/NH3 in CHCl3 ] to yield 71 mg (53%) of the title compound as a glass.

Workup

  1. temperaturewas heated at 60°-70° C
  2. extractionextracted four times with CH2Cl2
  3. washThe combined organic portions were washed once with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via flash chromatography [5→6% MeOH/NH3 in CHCl3 ]

Sources & evidence

ORD record
ord-4d452883254a4064807fd9fa314252e8
Source dataset
uspto-grants-1992_02
Patent number
US05089496

Reaction notes

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