Potassium Carbonate → HCID 19908365, compound

HRID 1534886Notes

Reaction equation

HRID 1534886 reaction equation
[NH2:1][C:2]([CH2:4][C:5]12[CH2:11][N:8]([CH2:9][CH2:10]1)[CH2:7][CH2:6]2)=[O:3].[C:12]1(=O)[O:16][CH:15]=[CH:14][O:13]1.[C:18](=[O:21])([O-:20])[O-].[K+].[K+]>>[C:12]([OH:16])(=[O:13])[C:18]([OH:20])=[O:21].[O:3]1[CH:15]=[CH:14][N:1]=[C:2]1[CH2:4][C:5]12[CH2:11][N:8]([CH2:7][CH2:6]1)[CH2:9][CH2:10]2

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 13385Vinylene carbonateHCID 19908370HCID 19908370, compound

Product 1

HCID 19908365HCID 19908365, compoundYield 7%

Conditions

Temperature
120 °C

Procedure

4(Aminocarbonylmethyl)-1-azabicyclo[2.2.1]heptane (D27) (350mg, 0.00227 mole) in polyphosphoric acid (15g) was treated with vinylene carbonate (292mg, 0.0034 mole) with continuous stirring and the solution heated on an oil bath at 120° C. for 1.5h. The reaction was then allowed to cool and poured into aqueous saturated potassium carbonate solution. The product was recovered by extraction into chloroform. The organic phase was separated, dried over sodium sulphate and concentrated in vacuo to a gum (48mg). The gum was dissolved in ether, filtered through a short column of decolourising charcoal and treated with oxalic acid (25mg) in methanol. The solution was allowed to crystallise to afford the title compound (E14) (45mg, 0.00017 moles, 7%) as needles. M.pt. 140-143° C.

Workup

  1. temperatureto cool
  2. customThe product was recovered by extraction into chloroform
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo to a gum (48mg)
  6. dissolutionThe gum was dissolved in ether
  7. filtrationfiltered through a short column of decolourising charcoal
  8. additiontreated with oxalic acid (25mg) in methanol
  9. customto crystallise

Sources & evidence

ORD record
ord-0df92a2552304a22a7002cf8af54e5d1
Source dataset
uspto-grants-1992_02
Patent number
US05091397

Reaction notes

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