Chloride → HCID 19864281, compound

HRID 1199927Notes

Reaction equation

HRID 1199927 reaction equation
[Cl-:1].Br[C:3]1[C:12]2[CH2:11][CH2:10][N:9]([CH3:13])[CH2:8][CH:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[S:5][CH:4]=1>CN(C)C=O.[Cu]>[Cl:1][C:3]1[C:12]2[CH2:11][CH2:10][N:9]([CH3:13])[CH2:8][CH:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[S:5][CH:4]=1

Participants

5

Reactant 2

HCID 312ChlorideHCID 19864278HCID 19864278, compound

Product 1

HCID 19864281HCID 19864281, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

Anhydrous copper I chloride (0.68 g) was added to a stirred solution of 3-bromo-6-methyl-8-phenyl-5,6,7,8-tetrahydro-4H-thieno[2,3-d]azepine (1.0 g) in dry dimethylformamide under nitrogen. The mixture was heated to 120° for 5 hours, evaporated, water added and extracted with dichloromethane. The extracts were dried, filtered and evaporated and the residue chromatographed on silica, eluting with 1% methanol in dichloromethane, to give a crude product which contained 10% of the starting bromo- compound. Further purification using preparative reverse phase high pressure liquid chromatographed gave the pure title product, m.p. 67° C.

Workup

  1. temperatureThe mixture was heated to 120° for 5 hours
  2. customevaporated
  3. additionwater added
  4. extractionextracted with dichloromethane
  5. customThe extracts were dried
  6. filtrationfiltered
  7. customevaporated
  8. customthe residue chromatographed on silica
  9. washeluting with 1% methanol in dichloromethane
  10. customto give a crude product which
  11. customFurther purification
  12. customchromatographed

Sources & evidence

ORD record
ord-8f09f93c84e94ace87c1186d59ddd12e
Source dataset
uspto-grants-1990_02
Patent number
US04904653

Reaction notes

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