HCID 19826898, compound → HCID 19826900, compound

HRID 1086155Notes

Reaction equation

HRID 1086155 reaction equation
[Br:1][C:2]1[S:3][C:4](Br)=[C:5]2[CH:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:10][N:9]([CH3:18])[CH2:8][CH2:7][C:6]=12>C(O)(=O)C.[Zn]>[Br:1][C:2]1[S:3][CH:4]=[C:5]2[CH:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:10][N:9]([CH3:18])[CH2:8][CH2:7][C:6]=12

Participants

4

Reactant 1

HCID 19826898HCID 19826898, compound

Product 1

HCID 19826900HCID 19826900, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc powder (0.19 g) was added to a stirred solution of 1,3-dibromo-6-methyl-4-phenyl-5,6,7,8-tetrahydro-4H-thieno[3,4-d]azepine (0.58 g) in acetic acid (10 ml) and the mixture heated under reflux for 5 hours under nitrogen. The mixture was evaporated, water (20 ml), 0.880 ammonia solution (5 ml) added, and extracted with dichloromethane (2×20 ml). The extracts were dried, filtered, evaporated and the residue chromatographed (silica, 1% methanol in dichloromethane) to give 1-bromo-6-methyl-4-phenyl-5,6,7,8-tetrahydro-4H-thieno [3,4-d]azepine as an oil. Later column fractions contained 6-methyl-4-phenyl-5,6,7,8-tetrahydro-4H-thieno[3,4-d]azepine.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 5 hours under nitrogen
  3. customThe mixture was evaporated
  4. additionwater (20 ml), 0.880 ammonia solution (5 ml) added
  5. extractionextracted with dichloromethane (2×20 ml)
  6. customThe extracts were dried
  7. filtrationfiltered
  8. customevaporated
  9. customthe residue chromatographed (silica, 1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-3c453bbab02042deaceb4fd3ef142d28
Source dataset
uspto-grants-1991_07
Patent number
US05028602

Reaction notes

Loading…