Ethyl Bromide → HCID 54552365, compound

HRID 1195767Notes

Reaction equation

HRID 1195767 reaction equation
[NH:1]1[C:7]2=[C:8]3[C:13](=[N:14][C:15]4=[CH:16][CH:17]=[CH:18][C:5](=[C:6]24)[O:4][CH2:3][C:2]1=[O:19])[CH2:12][CH2:11][CH2:10][CH2:9]3.[CH3:20][C:21](C)([O-])C.[K+].BrCC>O1CCCC1>[CH2:20]([N:1]1[C:7]2=[C:8]3[C:13](=[N:14][C:15]4=[CH:16][CH:17]=[CH:18][C:5](=[C:6]24)[O:4][CH2:3][C:2]1=[O:19])[CH2:12][CH2:11][CH2:10][CH2:9]3)[CH3:21]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 9795016HCID 9795016, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 54552365HCID 54552365, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (5.0 g) in dry tetrahydrofuran (110 ml) was added potassium tert-butoxide (2.65 g). The mixture was stirred for 20 mins, bromoethane (5.88 ml) was added, and the reaction mixture was refluxed for 6.5 hrs. The reaction mixture was concentrated, diluted with saturated potassium carbonate solution, and extracted with ethyl acetate. The organic extractions were dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was adhered to silica and flash chromatographed (20% ethyl acetate/hexane) to yield 4.53 g (82%) of 1-ethyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one

Workup

  1. temperaturethe reaction mixture was refluxed for 6.5 hrs
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with saturated potassium carbonate solution
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extractions
  6. dry with materialwere dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-794f01d82f974c41ac99d1eef17275d4
Source dataset
uspto-grants-1992_05
Patent number
US05112829

Reaction notes

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