Potassium Hydroxide → 2,3,4,5-Tetrahydro-1,5-benzoxazepine

HRID 50980

Reaction equation

HRID 50980 reaction equation
[OH-].[K+].ClC[CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][C:8]1=O>C(O)CCC>[O:9]1[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:7][CH2:6][CH2:5][CH2:8]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 100360722(3H)-Benzoxazolone, 3-(3-chloropropyl)-

Product 1

HCID 5777522,3,4,5-Tetrahydro-1,5-benzoxazepineYield 54.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Powdered KOH (37.60 g, 0.67 mol) was added to a slurry of 3-(3-chloropropyl)-1,3-benzoxazol-2(3H)-one (35.75 g, 0.169 mol) in n-butanol (450 mL) under N2 gas and refluxed for 52 hours. The mixture was filtered and reduced to dryness under reduced pressure. The residue was taken up in H2O (500 mL) and extracted with ether (3×200 mL). The organic was washed with 10% HCl (2×200 mL), dried over MgSO4, and stripped of solvent under reduced pressure. Purification by flash chromatography (50% EtOAc in hexanes) yielded 13.72 g (54%) of 2,3,4,5-tetrahydro-1,5-benzoxazepine as a powder, m.p. 50-51° C. (M+H)+ 149.

Workup

  1. temperaturerefluxed for 52 hours
  2. filtrationThe mixture was filtered
  3. extractionextracted with ether (3×200 mL)
  4. washThe organic was washed with 10% HCl (2×200 mL)
  5. dry with materialdried over MgSO4
  6. customPurification by flash chromatography (50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-976260e899e04a89a7c17e9e744c8602
Source dataset
uspto-grants-2004_03
Patent number
US06713471B1

Linked notes

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