Water → 2,3,4,5-Tetrahydro-1,4-benzoxazepine

HRID 540348Notes

Reaction equation

HRID 540348 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][NH:10][C:9](=O)[CH2:8]1.O>CCOCC.O1CCCC1.C(OCC)(=O)C>[O:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][NH:10][CH2:9][CH2:8]1

Participants

7

Reactant 3

HCID 962WaterHCID 9198014,5-dihydro-1,4-benzoxazepin-3(2H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 218827752,3,4,5-Tetrahydro-1,4-benzoxazepineYield 90.5%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the suspension of lithium aluminium hydride (15.2 g, 0.4 mol) in 600 mL of ether was added a solution of 4,5-dihydro-1,4-benzoxazepin-3(2H)-one (16.3 g, 0.1 mol) in 60 mL of tetrahydrofuran at room temperature. After being heated with stirring under reflux overnight, water was added dropwise to quench the reaction at 0° C., The resulting mixture was diluted with ethyl acetate, and then filtered by a pad of celite. The filtrate was concentrated under reduced pressure, followed by the addition of hydrochloric acid ethyl acetate solution. The hydrochloride was collected by filtration, washed with ethyl acetate then ether, and then dried in vacuo to give 13.5 g of product. MS obsd. (ESI+) [(M+H)+] 150.

Workup

  1. temperatureAfter being heated
  2. temperatureunder reflux overnight
  3. customto quench
  4. customthe reaction at 0° C.
  5. filtrationfiltered by a pad of celite
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. additionfollowed by the addition of hydrochloric acid ethyl acetate solution
  8. filtrationThe hydrochloride was collected by filtration
  9. washwashed with ethyl acetate
  10. dry with materialether, and then dried in vacuo

Sources & evidence

ORD record
ord-211d2f2e0fba4bb7af15e05910860a84
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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