Sodium Hydroxide → HCID 19747228, compound

HRID 484315Notes

Reaction equation

HRID 484315 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[C:16](=[C:17]3[CH2:22][CH2:21][N:20](C(OCC(Cl)(Cl)Cl)=O)[CH2:19][CH2:18]3)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[CH2:9][CH2:8][C:7]=2[CH:31]=1)#[N:2].[OH-].[Na+]>[Zn].C(O)(=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[C:16](=[C:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[CH2:9][CH2:8][C:7]=2[CH:31]=1)#[N:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19747239HCID 19747239, compound

Product 1

HCID 19747228HCID 19747228, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Acetic acid (25 ml) was added to 1 g of 8-cyano-11-[1-(2,2,2-trichloroethoxycarbonyl)-4-piperidylidene]-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine to dissolve the latter, followed by the addition of 2.75 g of zinc powder. The resulting mixture was heated under stirring for 2.5 hours over an oil bath of 70°-80° C. After the reaction, the reaction mixture was basified with a sodium hydroxide solution and then extracted with chloroform. The extract was dried over anhydrous Na2SO4 and then filtered. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography on a silica gel column. From relevant fractions eluted with chloroform:methanol (10:1), 0.41 g of 8-cyano-11-(4-piperidylidene)-6,11-dihydro-5H-benzo[5.6]cyclohepta[1,2-b]pyridine was obtained (yield: 65%).

Workup

  1. dissolutionto dissolve the latter
  2. temperatureThe resulting mixture was heated
  3. customAfter the reaction
  4. extractionextracted with chloroform
  5. dry with materialThe extract was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by chromatography on a silica gel column
  9. washFrom relevant fractions eluted with chloroform:methanol (10:1)

Sources & evidence

ORD record
ord-fc49506b269740e0ab17bf9b221eb2df
Source dataset
uspto-grants-1993_07
Patent number
US05231101

Reaction notes

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