Acetic Anhydride → HCID 20362674, compound

HRID 1679365Notes

Reaction equation

HRID 1679365 reaction equation
[C:1]([CH2:3][CH2:4][N:5]1[C:11](=[O:12])[CH2:10][CH:9]([CH3:13])[C:8]2[CH:14]=[CH:15][CH:16]=[CH:17][C:7]=2[CH2:6]1)#[N:2].[C:18](OC(=O)C)(=[O:20])[CH3:19].C([O-])(=O)C.[Na+]>>[C:18]([NH:2][CH2:1][CH2:3][CH2:4][N:5]1[C:11](=[O:12])[CH2:10][CH:9]([CH3:13])[C:8]2[CH:14]=[CH:15][CH:16]=[CH:17][C:7]=2[CH2:6]1)(=[O:20])[CH3:19]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 20362668HCID 20362668, compound

Product 1

HCID 20362674HCID 20362674, compoundYield 74%

Procedure

A solution of 8 g. (0.034 moles) of 2-(2-cyanoethyl)-5-methyl-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one in 220 ml. of acetic anhydride is introduced into a 2-liter autoclave, 12 g. of anhydrous sodium acetate and approximately 5 g. of W-5 -Raney nickel, washed twice with 20 ml. of acetic anhydride, are added thereto. The reaction mixture is brought to a temperature of 50° C. and then stirred for 4 hours under a hydrogen pressure (initial pressure of 3.5 bars). The reaction mixture is filtered, the catalyst is washed with a little acetic anhydride and the solvent is evaporated in vacuo. The residual oil is suspended in water and the pH of the mixture is adjusted to 8 by the addition of aqueous sodium hydroxide solution. It is extracted with chloroform and the organic phase is washed with water and dried over anhydrous sodium sulfate. The syrup obtained after filtration and evaporation of the solvent in vacuo is purified by chromatography on a silica column. 7 g. (74% of theory) of syrupy 2-(3-acetamidopropyl)-5-methyl-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one are obtained.

Workup

  1. washof W-5 -Raney nickel, washed twice with 20 ml
  2. additionof acetic anhydride, are added
  3. customis brought to a temperature of 50° C.
  4. filtrationThe reaction mixture is filtered
  5. washthe catalyst is washed with a little acetic anhydride
  6. customthe solvent is evaporated in vacuo
  7. additionthe pH of the mixture is adjusted to 8 by the addition of aqueous sodium hydroxide solution
  8. extractionIt is extracted with chloroform
  9. washthe organic phase is washed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe syrup obtained
  12. filtrationafter filtration and evaporation of the solvent in vacuo
  13. customis purified by chromatography on a silica column

Sources & evidence

ORD record
ord-e4ffccd7e9cd4fd9af3b296860e356df
Source dataset
uspto-grants-1978_03
Patent number
US04080449

Reaction notes

Loading…