Water → HCID 86698000, compound

HRID 518839Notes

Reaction equation

HRID 518839 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][CH2:9][C:10]2=[O:15])[CH3:3].[N-:16]=[N+]=[N-].[Na+].O.C(=O)([O-])[O-].[K+].[K+]>C(O)(C(F)(F)F)=O>[CH3:1][CH:2]([O:4][C:5]1[C:6]2[CH2:7][CH2:8][CH2:9][C:10](=[O:15])[NH:16][C:11]=2[CH:12]=[CH:13][CH:14]=1)[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 33557Sodium AzideHCID 65455198HCID 65455198, compound

Product 1

HCID 86698000HCID 86698000, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 4.39 g of 5-(propan-2-yloxy)-3,4-dihydronaphthalen-1(2H)-one and 1.74 g of sodium azide in 70 ml of TFA is refluxed for 2 hours. The reaction medium is poured into 250 ml of water, brought to pH 7 by adding potassium carbonate and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated under reduced pressure. Purification is carried out by flash chromatography on silica gel (40-63 μm), elution being carried out with a mixture of dichloromethane and MeOH (100/0 to 90/10). 2.87 g of 6-(propan-2-yloxy)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one are obtained in the form of a beige solid.

Workup

  1. temperatureis refluxed for 2 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customPurification
  7. washis carried out by flash chromatography on silica gel (40-63 μm), elution
  8. additionbeing carried out with a mixture of dichloromethane and MeOH (100/0 to 90/10)

Sources & evidence

ORD record
ord-275103b7f83a4edcb27342591206dbdd
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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