Potassium Carbonate → HCID 178463246, compound

HRID 1155549Notes

Reaction equation

HRID 1155549 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([C:10](OCC)(OCC)[CH2:11][NH2:12])[CH:7]=[CH:6][N:5]=1)[CH3:2].Cl.[C:20](=[NH:25])(OCC)[CH3:21].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([C:10]2[N:25]=[C:20]([CH3:21])[NH:12][CH:11]=2)[CH:7]=[CH:6][N:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 131452922-(2-Ethylamino-4-pyridyl)-2,2-diethoxyethylamine

Product 1

HCID 178463246HCID 178463246, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.0 g. (8 mmoles) of 2-(2-ethylamino-4-pyridyl)-2,2-diethoxyethylamine, 1.0 g. (8.3 mmoles) of ethyl acetimidate hydrochloride and 30 ml. of absolute ethanol was heated at reflux for 1.3 hours. The mixture was concentrated, and the residue taken up in 10 ml. of concentrated hydrochloric acid. The acid solution was heated on a steam bath for one hour and the cooled reaction made basic by the addition of solid potassium carbonate. The product was extracted with chloroform (4×15 ml.) and the combined extracts dried and concentrated to give 1.1 g. of crude product. The product was chromatographed over 35 g. of silica gel using chloroform-methanol (19:1, v:v) as the eluent to give 510 mg. (30%), m.p. 214°-216° C.

Workup

  1. additionA mixture of 2.0 g
  2. temperatureat reflux for 1.3 hours
  3. concentrationThe mixture was concentrated
  4. temperatureThe acid solution was heated on a steam bath for one hour
  5. customthe cooled reaction
  6. extractionThe product was extracted with chloroform (4×15 ml.)
  7. customthe combined extracts dried
  8. concentrationconcentrated
  9. customto give 1.1 g
  10. customThe product was chromatographed over 35 g
  11. customto give 510 mg

Sources & evidence

ORD record
ord-97c6c99067124e5980625e23cf751e4c
Source dataset
uspto-grants-1981_11
Patent number
US04302464

Reaction notes

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