1-Bromopropane → 10-Propyl-dibenz(b,f)(1,4)oxazepin-11-(10H)-one

HRID 1898862Notes

Reaction equation

HRID 1898862 reaction equation
[CH:1]1[C:6]2[C:7](=[O:16])[NH:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:20][CH2:21][CH3:22]>CN(C)C=O>[CH2:20]([N:8]1[C:7](=[O:16])[C:6]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[O:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]1=2)[CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 24758Sodium hydride2×HCID 72374O-(o-Aminophenoxy)benzoic acid lactam

Product 1

HCID 45391710-Propyl-dibenz(b,f)(1,4)oxazepin-11-(10H)-oneYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3.0 grams of 10H-dibenz[b,f][1,4]oxazepin-11-one in 50 ml of dry dimethylformamide was added 0.82 grams of a 50% dispersion of sodium hydride in mineral oil. The resulting mixture was stirred for one hour and 3.7 grams of 1-bromopropane was then added slowly. The reaction mixture was stirred for 3 hours and the excess sodium hydride decomposed by the addition of ice. After further dilution with water the product was extracted with ether, dried (anhydrous sodium sulfate) and concentrated. The resulting oil was purified on a silica gel column (ethyl acetate/hexane, 1:4) to provide 3.1 grams (87% of theory) of 10-propyl-10H-dibenz[b,f][1.4]oxazepin-11-one as a colorless oil.

Workup

  1. stirringThe reaction mixture was stirred for 3 hours
  2. extractionAfter further dilution with water the product was extracted with ether
  3. dry with materialdried (anhydrous sodium sulfate)
  4. concentrationconcentrated
  5. customThe resulting oil was purified on a silica gel column (ethyl acetate/hexane, 1:4)

Sources & evidence

ORD record
ord-b1898d6743084b4f925bc7cce0567ab6
Source dataset
uspto-grants-1996_11
Patent number
US05571806

Reaction notes

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