Potassium Hydroxide → HCID 19747323, compound

HRID 484312Notes

Reaction equation

HRID 484312 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]([CH3:23])[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:24]=1)#[N:2].[OH-:25].[K+]>C(O)C>[CH3:23][N:20]1[CH2:21][CH2:22][C:17](=[C:16]2[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[CH2:9][CH2:8][C:7]3[CH:24]=[C:3]([C:1]([NH2:2])=[O:25])[CH:4]=[CH:5][C:6]2=3)[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 307264811-(1-Methylpiperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine-8-carbonitrile

Product 1

HCID 19747323HCID 19747323, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethanol (150 ml) was added to 2 g of 8-cyano-11-(1-methyl-4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine so that the latter was dissolved in the former. An aqueous solution of 2.8 g of potassium hydroxide was added further, followed by reflux for 3.5 hours. After the reaction, the solvent was distilled off under reduced pressure and a brine was added to the residue, followed by extraction with chloroform. The extract was dried over anhydrous Na2SO4 and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column and, from relevant fractions eluted with chloroform:methanol 25:1 and 10:1), 1.4 g of 11-(1-methyl-4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine-8-carboxamide were obtained (yield: 66%).

Workup

  1. dissolutionwas dissolved in the former
  2. temperatureby reflux for 3.5 hours
  3. customAfter the reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. additiona brine was added to the residue
  6. extractionfollowed by extraction with chloroform
  7. dry with materialThe extract was dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customThe residue was purified by chromatography on a silica gel column and, from relevant fractions
  11. washeluted with chloroform:methanol 25:1 and 10:1), 1.4 g of 11-(1-methyl-4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine-8-carboxamide
  12. customwere obtained (yield: 66%)

Sources & evidence

ORD record
ord-b42b2f3b98584253b8da0faf4292356c
Source dataset
uspto-grants-1993_07
Patent number
US05231101

Reaction notes

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