Methyl Ethyl Ketone → N-(1-ethyl-2-pyrrolidylmethyl)-8-methoxy-1,4-benzodioxane-5-carboxamide

HRID 127425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 127425
[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH2:9])[CH3:2].C(C(C)=O)C.[CH3:15][O:16][C:17]1[C:22]2[O:23][CH2:24][CH2:25][O:26][C:21]=2[C:20]([C:27](Cl)=[O:28])=[CH:19][CH:18]=1>O>[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH:9][C:27]([C:20]1[C:21]2[O:26][CH2:25][CH2:24][O:23][C:22]=2[C:17]([O:16][CH3:15])=[CH:18][CH:19]=1)=[O:28])[CH3:2]

Komponenten

5

Edukt 3

HCID 6569Methyl Ethyl KetoneHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 205447108-Methoxy-1,4-benzodioxane-5-carbonyl chloride

Produkt 1

HCID 53981082N-(1-ethyl-2-pyrrolidylmethyl)-8-methoxy-1,4-benzodioxane-5-carboxamideAusbeute 103,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

87 g of 1-ethyl-2-aminomethyl pyrrolidine and 775 cm3 of methyl ethyl ketone were introduced into a balloon flask provided with an agitator and a thermometer and then, in portions, 155 g of 8-methoxy-1,4-benzodioxane-5-carbonyl chloride was added, with the temperature being maintained at from 5°-10° C. After agitation the mixture was dissolved with 1,500 cm3 of water and then the methyl ethyl ketone was distilled. The remaining solution was filtered and then treated with sodium hydroxide. The oil was decanted and then extracted with methylene chloride. The solution was dried on potassium carbonate and then the methylene chloride was distilled under vacuum. 224.5 g of N-(1-ethyl-2-pyrrolidylmethyl)-8-methoxy-1,4-benzodioxane-5-carboxamide was produced. 197.5 g of the base produced was dissolved in 760 cm3 of absolute alcohol, and then 67 g of oxalic acid in solution in 195 cm3 of absolute alcohol was added. The crystals formed were dried off, washed with absolute alcohol and then dried. 208.5 g of N-(1-ethyl-2-pyrrolidylmethyl)-8-methoxy-1,4-benzodioxane-5-carboxamide oxalate was produced (M.P. 129°-130° C.; yield: 82%).

Aufarbeitung

  1. customprovided with an agitator
  2. temperaturebeing maintained at from 5°-10° C
  3. distillationthe methyl ethyl ketone was distilled
  4. filtrationThe remaining solution was filtered
  5. additiontreated with sodium hydroxide
  6. customThe oil was decanted
  7. extractionextracted with methylene chloride
  8. customThe solution was dried on potassium carbonate
  9. distillationthe methylene chloride was distilled under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-875afc75d55143fcb0e92254537d757d
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04255580

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