Sulfuric Acid → HCID 19747226, compound

HRID 484313Notes

Reaction equation

HRID 484313 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]2[C:18]([CH:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)(O)[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[CH2:11][CH2:10][C:9]=2[CH:27]=1)(=[O:4])=[O:3].OS(O)(=O)=O.C(S(O)(=O)=O)(F)(F)F.[OH-].[Na+]>>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]2[C:18](=[C:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[CH2:11][CH2:10][C:9]=2[CH:27]=1)(=[O:3])=[O:4]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 19747266HCID 19747266, compound

Product 1

HCID 19747226HCID 19747226, compoundYield 74%

Procedure

To 1.35 g of 8-methylsulfonyl-6,11-dihydro-11-(1-methyl-4-piperidyl)-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ol, 24 ml of a mixed solution of conc. H2SO4 and CF3SO3H (2:1) were added. The resultant mixture was stirred at 50° C. for 5 hours. After the reaction, the reaction mixture was poured into ice water, basified with a 20% sodium hydroxide solution and then extracted with methylene chloride. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous MgSO4 and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by chromatography on an alumina column, whereby 0.95 g of 8-methylsulfonyl-11-(1-methyl-4-piperidylidene)-6,11-dihydro-5H-benzo]5,6]cyclohepta[1,2-b]pyridine was obtained (yield: 74%).

Workup

  1. customAfter the reaction
  2. extractionextracted with methylene chloride
  3. washThe extract was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by chromatography on an alumina column, whereby 0.95 g of 8-methylsulfonyl-11-(1-methyl-4-piperidylidene)-6,11-dihydro-5H-benzo]5,6]cyclohepta[1,2-b]pyridine
  8. customwas obtained (yield: 74%)

Sources & evidence

ORD record
ord-b65de0a6ad13470497dfc27db6639941
Source dataset
uspto-grants-1993_07
Patent number
US05231101

Reaction notes

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