HCID 59438395, compound → HCID 59438473, compound

HRID 2177479Notes

Reaction equation

HRID 2177479 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([N+:16]([O-])=O)[CH2:13][N:12]([CH3:14])[C:11](=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1>O1CCOCC1.[Zn]>[NH2:16][C:8]1([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH2:13][N:12]([CH3:14])[C:11](=[O:15])[CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 59438395HCID 59438395, compound

Product 1

HCID 59438473HCID 59438473, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 115 mg (0.428 mmol) 5-(3-chloro-phenyl)-1-methyl-5-nitro-piperidin-2-one in 0.5 ml dioxane was added 2 ml 3NHCl and 280 mg (4.28 mmol) zinc dust. The mixture was stirred at room temperature for 30 minutes. The mixture was filtered and the filtrate was basified with a 5N NaOH solution. Ethyl acetate was added. The mixture was filtered through a pad of dicalite. The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. The combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo to provide 88 mg (86%) of the title compound as a light yellow oil. MS (m/e): 239.0 (MH+).

Workup

  1. filtrationThe mixture was filtered
  2. additionEthyl acetate was added
  3. filtrationThe mixture was filtered through a pad of dicalite
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted twice with ethyl acetate
  6. dry with materialThe combined extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d14da63c72544501b4015d50aeee3c73
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

Loading…