Carbon Dioxide → HCID 178487436, compound

HRID 1643241Notes

Reaction equation

HRID 1643241 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C@@H:13]1[CH2:18][O:17][C@@H:16]([CH2:19][CH2:20][CH2:21][NH2:22])[O:15][CH2:14]1)=[CH:8][CH:7]=[CH:6]2.[C:23](=[O:26])([O-])[O-:24].[Cs+].[Cs+].C(=O)=O.Cl[CH2:33][C:34]([NH2:36])=[O:35]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C@@H:13]1[CH2:14][O:15][C@@H:16]([CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:26])[O:24][CH2:33][C:34]([NH2:36])=[O:35])[O:17][CH2:18]1)=[CH:8][CH:7]=[CH:6]2

Participants

7

Reactant 4

HCID 280Carbon Dioxide2×HCID 6580ChloroacetamideHCID 10796Cesium carbonateHCID 178487437HCID 178487437, compound

Product 1

HCID 178487436HCID 178487436, compoundYield 24.5%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent2×

Procedure

20 g (66 mmol) of trans-3-[5-(6-methoxynaphthalen-1-yl)-1,3-dioxan-2-yl]propanamine, 64 g (198 mmol) of cesium carbonate and 73.14 g (198 mmol) of tetra-n-butylammonium iodide in suspension in 400 ml of N,N-dimethylformamide are introduced into a 1 l three-necked round-bottomed flask placed under an inert atmosphere. A stream of carbon dioxide is passed through the suspension, with vigorous stirring, for 2 h. 18.5 g (198 mmol) of chloroacetamide in solution in 70 ml of N,N-dimethylformamide are then added dropwise, and the stream of carbon dioxide is maintained for 5 h, and the stirring is continued at ambient temperature overnight. The salts are separated by filtration, the filtrate is concentrated under reduced pressure, the residue is taken up with ethyl acetate and water, and the organic phase is separated and washed with a 0.1N aqueous hydrochloric acid solution, then a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution. The organic phase is dried over sodium sulfate and the filtrate is concentrated under reduced pressure, the residue is purified by chromatography on silica gel, eluting with a 95/5 mixture of ethyl acetate and methanol, and the solid obtained is recrystallized from ethyl acetate to obtain 6.5 g of pure product.

Workup

  1. customThe salts are separated by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customthe organic phase is separated
  4. washwashed with a 0.1N aqueous hydrochloric acid solution
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customthe residue is purified by chromatography on silica gel
  8. washeluting with a 95/5 mixture of ethyl acetate and methanol
  9. customthe solid obtained
  10. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ebe84fa6b4284d4284e8b5d57a2952fd
Source dataset
uspto-grants-2012_02
Patent number
US08119687B2

Reaction notes

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