Acetic Anhydride → HCID 19747243, compound

HRID 484316Notes

Reaction equation

HRID 484316 reaction equation
[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:23]=1)#[N:2].[C:24](OC(=O)C)(=[O:26])[CH3:25]>N1C=CC=CC=1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[C:16](=[C:17]3[CH2:22][CH2:21][N:20]([C:24](=[O:26])[CH3:25])[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:23]=1)#[N:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 19747228HCID 19747228, compound

Product 1

HCID 19747243HCID 19747243, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Pyridine (4 ml) was added to 0.4 g of 8-cyano-11-(4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine to dissolve the latter, followed by the addition of 8 ml of acetic anhydride. At the room temperature, the resulting mixture was stirred for 4 hours. After the completion of the reaction, the reaction mixture was concentrated under reduced pressure. Water was added to the residue, followed by extraction with chloroform. The extract was next dried over anhydrous Na2SO4 and the chloroform was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column and, from relevant fractions eluted with chloroform:methanol (100:1), 0.3 g of 8-cyano-11-(1-acetyl-4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine was obtained (yield: 66%).

Workup

  1. dissolutionto dissolve the latter
  2. customAfter the completion of the reaction
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. additionWater was added to the residue
  5. extractionfollowed by extraction with chloroform
  6. dry with materialThe extract was next dried over anhydrous Na2SO4
  7. distillationthe chloroform was distilled off under reduced pressure
  8. customThe residue was purified by chromatography on a silica gel column and, from relevant fractions
  9. washeluted with chloroform:methanol (100:1)

Sources & evidence

ORD record
ord-349a211e68d34080b147b13b0aa368f3
Source dataset
uspto-grants-1993_07
Patent number
US05231101

Reaction notes

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