Sodium Carbonate → HCID 9925529, compound

HRID 1836949Notes

Reaction equation

HRID 1836949 reaction equation
[C:1]1([CH:7]([O:9][C:10]([N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[O:11])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl.N[CH:20]1[CH:25]2CCN(C[CH2:24]2)[CH2:21]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[C:1]1([CH:7]([O:9][C:10](=[O:11])[NH:12][CH:16]2[CH:25]3[CH2:24][CH2:13][N:14]([CH2:21][CH2:20]3)[CH2:15]2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 197853Quinuclidine, 3-amino-, dihydrochlorideHCID 11298884HCID 11298884, compound

Product 1

HCID 9925529HCID 9925529, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of imidazole-1-carboxylic acid 1-phenyl-ethyl ester 0.50 g (2.31 mmol) in 5 ml dimethylformamide, 3-aminoquinuclidine dihydrochloride 0.46 g (2.31 mmol) and sodium carbonate 0.49 g (4.62 mmol) are added. The suspension is heated up to 80° C. and stirred for 18 hours at this temperature. The reaction mixture is then cooled and extracted with water and ethylacetate. The combined organic phases are dried and evaporated. The oily residue is dried, dissolved in ether and acidified with a 4 M hydrochloric acid dioxane solution. The precipitating crystals are filtered, washed with ether and dried to give the title product. Mp=71-72° C. (decomposition).

Workup

  1. temperatureThe reaction mixture is then cooled
  2. extractionextracted with water and ethylacetate
  3. customThe combined organic phases are dried
  4. customevaporated
  5. customThe oily residue is dried
  6. dissolutiondissolved in ether
  7. filtrationThe precipitating crystals are filtered
  8. washwashed with ether
  9. customdried

Sources & evidence

ORD record
ord-fa50705564bf47c9a4dc03e81af6af01
Source dataset
uspto-grants-2004_08
Patent number
US06780861B2

Reaction notes

Loading…