HCID 19826902, compound → HCID 19826887, compound

HRID 1086154Notes

Reaction equation

HRID 1086154 reaction equation
Cl.Br[C:3]1[S:4][C:5](Br)=[C:6]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][N:10]([CH3:19])[CH2:9][CH2:8][C:7]=12>C(O)(=O)C.[Zn]>[CH3:19][N:10]1[CH2:11][CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:6]2=[CH:5][S:4][CH:3]=[C:7]2[CH2:8][CH2:9]1

Participants

4

Reactant 1

HCID 19826902HCID 19826902, compound

Product 1

HCID 19826887HCID 19826887, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

Zinc powder (0.73 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 hydrochloride (0.98 g) in acetic acid (20 ml) under nitrogen and the mixture heated under reflux. Further portions of zinc powder (0.73 g) were added after 2 hours and 20 hours heating. After a total of 24 hours heating the mixture was evaporated, water (30 ml) 0.880 ammonia solution (10 ml) added, and extracted with dichloromethane (2×30 ml). The extracts were dried, filtered and evaporated to a yellow oil. Chromatography on silica (2% methanol in dichloromethane) gave the title product as a colourless oil. 1H NMR o(CDCl3) 7.24-7.39 (5H,m,ArH), 6.92 (lH,d,J=3.1 Hz, H1), 6.25 (lH,d,J=3.1 Hz, H3), 4.17 (lH,d,J=9.7 Hz, PhCH), 2.80-3.06 (5H,m,5-CH2 -CHeq 8-CH2), 2.45 (3H,s, NCH3), 2.30-2.50 (lH,m,7-CHax).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux
  3. temperatureheating
  4. temperatureAfter a total of 24 hours heating the mixture
  5. customwas evaporated
  6. additionwater (30 ml) 0.880 ammonia solution (10 ml) added
  7. extractionextracted with dichloromethane (2×30 ml)
  8. customThe extracts were dried
  9. filtrationfiltered
  10. customevaporated to a yellow oil

Sources & evidence

ORD record
ord-1959ef3b4ee4452997437d4568c302f8
Source dataset
uspto-grants-1991_07
Patent number
US05028602

Reaction notes

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