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

HRID 2052645Notes

Reaction equation

HRID 2052645 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-b4d4477c9f0d42308ef7b332bd16932b
Source dataset
uspto-grants-1980_01
Patent number
US04186135

Reaction notes

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