HCID 10098451, compound → HCID 11757152, compound

HRID 2108108Notes

Reaction equation

HRID 2108108 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:36][CH3:37])=[CH:5][C:6]2[S:12][CH2:11][CH2:10][C:9]([C:13]([N:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:34])[C:22]4[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=4)[CH2:17][CH2:16]3)=[O:14])=[CH:8][C:7]=2[CH:35]=1.I([O-])(=O)(=O)=[O:39].[Na+]>CO.O>[CH3:1][O:2][C:3]1[C:4]([O:36][CH3:37])=[CH:5][C:6]2[S:12](=[O:39])[CH2:11][CH2:10][C:9]([C:13]([N:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:34])[C:22]4[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=4)[CH2:17][CH2:16]3)=[O:14])=[CH:8][C:7]=2[CH:35]=1

Participants

5

Reactant 2

HCID 10098451HCID 10098451, compoundHCID 23667635Sodium periodate

Product 1

HCID 11757152HCID 11757152, compoundYield 78.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In methanol (10 ml) is dissolved 1-(7,8-dimethoxy-2,3-dihydro-1-benzothiepin-4-carbonyl)-4-(3,4,5-trimethoxybenzoyl)piperazine (1.6 g) obtained in Working Example 24. To the solution is added dropwise, while stirring under ice-cooling, a solution of sodium periodate (960 mg) in water (1 ml). The mixture is stirred for one hour under ice-cooling, and left standing for 48 hours at -5° C. Resultant precipitates are filtered off. To the filtrate is added water, followed by extraction with methylene chloride. The organic layer is washed with an aqueous solution of sodium hydrogencarbonate, dried, and concentrated under reduced pressure. The residue is recrystallized from ethanol-ether to give 1-(7,8-dimethoxy-1-oxo-2,3-dihydro1-benzothiepin-4-carbonyl)-4-(3,4,5-trimethoxybenzoyl)piperazine as colorless prisms (1.3 g), m.p. 138° C.

Workup

  1. customobtained in Working Example 24
  2. additionTo the solution is added dropwise
  3. temperaturecooling
  4. stirringThe mixture is stirred for one hour under ice-
  5. temperaturecooling
  6. waitleft
  7. customResultant precipitates
  8. filtrationare filtered off
  9. additionTo the filtrate is added water
  10. extractionfollowed by extraction with methylene chloride
  11. washThe organic layer is washed with an aqueous solution of sodium hydrogencarbonate
  12. customdried
  13. concentrationconcentrated under reduced pressure
  14. customThe residue is recrystallized from ethanol-ether

Sources & evidence

ORD record
ord-83bc811f3b164da6ad93f37ef30c7669
Source dataset
uspto-grants-1990_06
Patent number
US04937246

Reaction notes

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