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

HRID 1413166

반응식

HRID 1413166 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 53981082N-(1-ethyl-2-pyrrolidylmethyl)-8-methoxy-1,4-benzodioxane-5-carboxamide수율 103.4%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-1a9aeacbacac403eaa427a532c4b504b
출처 데이터셋
uspto-grants-1981_02
특허 번호
US04248885

연결된 노트

불러오는 중…