Ammonium Chloride → HCID 23565319, compound

HRID 1059279Notes

Reaction equation

HRID 1059279 reaction equation
[CH3:1][N:2]1[CH2:9][CH:8]2[C:10](=[CH:11][C:12]([O:14][CH2:15]C)=[O:13])[CH:4]([CH2:5][CH2:6][CH2:7]2)[CH2:3]1.[Mg].[Cl-].[NH4+]>CO>[CH3:1][N:2]1[CH2:9][CH:8]2[CH:10]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:4]([CH2:5][CH2:6][CH2:7]2)[CH2:3]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 72974170HCID 72974170, compound

Product 1

HCID 23565319HCID 23565319, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

37.13 g of ethyl (3-methyl-3-azabicyclo[3.3.1]non-9-ylidene)acetate was dissolved in 815 ml of methanol. After adding 20.24 g of magnesium, the resulting mixture was stirred at room temperature for 18 hours. Then a saturated aqueous solution of ammonium chloride was added to the reaction mixture followed by extraction with ethyl acetate. The ethyl acetate layer was washed successively with water and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After concentrating the solvent under reduced pressure, 34.32 g of crude methyl (3-methyl-3-azabicyclo[3.3.1]non-9-yl)acetate was obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe ethyl acetate layer was washed successively with water
  3. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  4. concentrationAfter concentrating the solvent under reduced pressure

Sources & evidence

ORD record
ord-8e2ce3d588584fe4a3ec27a392787bb3
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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