Potassium Carbonate → 1,3,4,5-Tetrahydro-6-(2-oxiranylmethoxy)-2H-1-benzazepin-2-one

HRID 1759312Notes

Reaction equation

HRID 1759312 reaction equation
[OH:1][C:2]1[C:7]2[CH2:8][CH2:9][CH2:10][C:11](=[O:13])[NH:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:14]([CH:16]1[O:18][CH2:17]1)Br.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C(C)C>[O:18]1[CH2:17][CH:16]1[CH2:14][O:1][C:2]1[C:7]2[CH2:8][CH2:9][CH2:10][C:11](=[O:13])[NH:12][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 99422906-Hydroxy-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

Product 1

HCID 232893091,3,4,5-Tetrahydro-6-(2-oxiranylmethoxy)-2H-1-benzazepin-2-oneYield 60%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

5.3 g (0.03 mole) of 6-hydroxy-2,3,4,5-tetrahydro-1H-benzazepin-2-one, 5 ml of epibromohydrin and 4.5 g of potassium carbonate in 250 ml of methyl isobutyl ketone are refluxed for 48 hours. After the mixture has cooled, it is filtered and the filtrate is concentrated under reduced pressure on a rotary evaporator. The residue is recrystallized from cyclohexane in the presence of animal charcoal. 4.2 g (60% yield) of 6-(2,3-epoxy-propoxy)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one, of melting point 121°-123° C., are obtained.

Workup

  1. temperatureAfter the mixture has cooled
  2. filtrationit is filtered
  3. concentrationthe filtrate is concentrated under reduced pressure on a rotary evaporator
  4. customThe residue is recrystallized from cyclohexane in the presence of animal charcoal

Sources & evidence

ORD record
ord-0225836f782542a790b19ea8bf85e5a3
Source dataset
uspto-grants-1982_07
Patent number
US04340595

Reaction notes

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