N-bromobutanimide → HCID 9944801, compound

HRID 1057366Notes

Reaction equation

HRID 1057366 reaction equation
[C:1]([O:5][C:6]([CH:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[CH:18][C:11]=2[N:10]([CH2:21][CH3:22])[C:9]1=[O:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].BrN1C(=O)CCC1=O>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([CH:8]1[CH:14]=[CH:13][C:12]2[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[CH:18][C:11]=2[N:10]([CH2:21][CH3:22])[C:9]1=[O:23])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 9836705HCID 9836705, compound

Product 1

HCID 9944801HCID 9944801, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 3(R,S)-tert-butoxycarbonyl-1-ethyl-8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepine-2-one (0.80 g, 2.51 mmol) and N-bromosuccinimide (0.49 g, 2.76 mmol) in chloroform (20 mL) was heated at reflux for 5 hrs. The resulting reaction mixture was washed with saturated aqueous solution of NaHCO3 and water, dried over anhydrous Na2SO4, filtered and evaporated to dryness. The crude product was purified by flash chromatography on silica gel column eluted with EtOAc/n-hexane (3:7). The fractions containing the fast running component were collected and evaporated to dryness. The desired compound (60 mg, 8%) was obtained as a white crystalline powder.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hrs
  3. customThe resulting reaction mixture
  4. washwas washed with saturated aqueous solution of NaHCO3 and water
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe crude product was purified by flash chromatography on silica gel column
  9. washeluted with EtOAc/n-hexane (3:7)
  10. additionThe fractions containing the
  11. customwere collected
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-4dcbfef69a7342609f91a7630cd7f0c5
Source dataset
uspto-grants-2003_02
Patent number
US06514965B1

Reaction notes

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