Thionyl Chloride → 11-(1-Methylpiperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine-8-carbonitrile

HRID 484311Notes

Reaction equation

HRID 484311 reaction equation
S(Cl)(Cl)=O.[C:5]([C:7]1[CH:8]=[CH:9][C:10]2[C:20]([CH:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)(O)[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[CH2:13][CH2:12][C:11]=2[CH:29]=1)#[N:6]>>[C:5]([C:7]1[CH:8]=[CH:9][C:10]2[C:20](=[C:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[CH2:13][CH2:12][C:11]=2[CH:29]=1)#[N:6]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 19747289HCID 19747289, compound

Product 1

HCID 307264811-(1-Methylpiperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine-8-carbonitrileYield 63%

Procedure

Thionyl chloride (15 ml) was added to 2.7 g of 8-cyano-6,11-dihydro-11-(1-methyl-4-piperidyl)-5H-benzo[ 5,6]cyclohepta[1,2-b]pyridin-11-ol, followed by reflux for 8 hours. The reaction mixture was concentrated under reduced pressure. An aqueous solution of sodium hydroxide was added to the residue to render the latter basic, followed by extraction with chloroform. The extract was dried over anhydrous Na2SO4 and filtered and 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 (50:1), 1.6 g of 8-cyano-11-(1-methyl-4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine were obtained (yield: 63%).

Workup

  1. temperatureby reflux for 8 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionAn aqueous solution of sodium hydroxide was added to the residue
  4. extractionfollowed by extraction 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 and, from relevant fractions
  9. washeluted with chloroform:methanol (50:1)

Sources & evidence

ORD record
ord-b2d37218f2cd4b3c8bca6b998800cc84
Source dataset
uspto-grants-1993_07
Patent number
US05231101

Reaction notes

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