Toluene → HCID 19747296, compound

HRID 484314Notes

Reaction equation

HRID 484314 reaction equation
C1(C)C=CC=CC=1.[C:8]([C:10]1[CH:11]=[CH:12][C:13]2[C:23](=[C:24]3[CH2:29][CH2:28][N:27](C)[CH2:26][CH2:25]3)[C:18]3=[N:19][CH:20]=[CH:21][CH:22]=[C:17]3[CH2:16][CH2:15][C:14]=2[CH:31]=1)#[N:9].Cl[C:33]([O:35][CH2:36][CH3:37])=[O:34]>C(N(CC)CC)C>[C:8]([C:10]1[CH:11]=[CH:12][C:13]2[C:23](=[C:24]3[CH2:29][CH2:28][N:27]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:26][CH2:25]3)[C:18]3=[N:19][CH:20]=[CH:21][CH:22]=[C:17]3[CH2:16][CH2:15][C:14]=2[CH:31]=1)#[N:9]

Participants

5

Reactant 3

HCID 1140TolueneHCID 10928Ethyl chloroformateHCID 307264811-(1-Methylpiperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine-8-carbonitrile

Product 1

HCID 19747296HCID 19747296, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Toluene (40 ml) was added to 1 g of 8-cyano-11-(1-methyl-4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine to dissolve the latter, followed by the addition of 0.52 g of triethylamine and 1.92 g of ethyl chloroformate. The resulting mixture was refluxed for 2.5 hours. The mixture was cooled and washed with water. The organic layer 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. The substance eluted with chloroform was recrystallized from n-hexane, whereby 0.89 g of 8-cyano-11-(1-ethoxycarbonyl-4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine was obtained (yield: 75%).

Workup

  1. dissolutionto dissolve the latter
  2. temperatureThe resulting mixture was refluxed for 2.5 hours
  3. temperatureThe mixture was cooled
  4. washwashed with water
  5. dry with materialThe organic layer 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. washThe substance eluted with chloroform
  10. customwas recrystallized from n-hexane

Sources & evidence

ORD record
ord-6c41ce57016f4224b25be82891c727b6
Source dataset
uspto-grants-1993_07
Patent number
US05231101

Reaction notes

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