Potassium Carbonate → HCID 70206772, compound

HRID 611567Notes

Reaction equation

HRID 611567 reaction equation
[ClH:1].Cl.[NH:3]1[CH2:7][CH2:6][CH2:5][C@H:4]1[C:8]1[O:16][C:11]2=[CH:12][N:13]=[CH:14][CH:15]=[C:10]2[CH:9]=1.[C:17]([O-])([O-])=O.[K+].[K+]>C(O)=O.C=O>[ClH:1].[ClH:1].[CH3:17][N:3]1[CH2:7][CH2:6][CH2:5][C@H:4]1[C:8]1[O:16][C:11]2=[CH:12][N:13]=[CH:14][CH:15]=[C:10]2[CH:9]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 70204345HCID 70204345, compound

Product 1

HCID 70206772HCID 70206772, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 712FormaldehydeSolvent

Procedure

A 120 mg sample of the compound from Example 9 above was dissolved in 4 mL of formic acid and 2 mL of formalin, and the reaction mixture was heated at reflux for 30 minutes. The reaction mixture was cooled to ambient temperature and poured into saturated K2CO3 solution. The resulting mixture was extracted with CH2Cl2, the extract was dried, and the solvent was removed. The residue was chromatographed on silica gel, and the compound was converted to the salt by treatment with HCl/ether: 1H NMR (D2O, 300 MHz) δ 2.30-2.40 (m, 3H), 2.50-2.74 (m, 1H), 2.98 (s, 3H), 3.45 (br d, 1H), 3.85 (br s, 1H), 4.97 (t, 1H), 7.47 (s, 1H), 8.08 (d, 1H), 8.51 (d, 1H), 9.10 (s, 1H); MS m/z: 203 (M+H)+ ; Anal. Calcd for C12H14N2O·2 HCl.0.5H2O: C, 50.70; H, 6.03; N, 9.86. Found: C, 50.69; H, 6.09; N, 9.61.

Workup

  1. temperatureat reflux for 30 minutes
  2. extractionThe resulting mixture was extracted with CH2Cl2
  3. customthe extract was dried
  4. customthe solvent was removed
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-034acf24d6cb41bfb4ce2ca6f420c28d
Source dataset
uspto-grants-1999_12
Patent number
US06001849

Reaction notes

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