Acetone → HCID 70550692, compound

HRID 2286942Notes

Reaction equation

HRID 2286942 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH2:9])[CH3:2].C1[C:19]2[C:11]1=[C:12]([CH:16]=[C:17]([OH:21])[C:18]=2O)[C:13]([Cl:15])=[O:14].Cl.C[C:24](C)=[O:25]>C(Cl)(Cl)Cl.O>[ClH:15].[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH:9][C:13](=[O:14])[C:12]1[CH:11]=[CH:19][CH:18]=[C:17]2[O:21][CH2:24][O:25][C:16]=12)[CH3:2]

Participants

7

Reactant 4

HCID 180Acetone2×HCID 313Hydrochloric AcidHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 131711712HCID 131711712, compound

Product 1

HCID 70550692HCID 70550692, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

134 g of 1-ethyl-2-aminomethyl-pyrrolidine, 950 cm3 of chloroform and, gradually, 183 g of 2,3-methylenedioxyl benzoyl chloride, with the temperature being maintained at from 5°-10° C., were introduced into a balloon flask provided with an agitator and a thermometer. After the addition of 1 liter of water, chloroform was distilled and then the remaining solution was filtered. After the addition of 120 cm3 of 20% ammonia and extraction with ether, the ethereal solution was dried on potassium carbonate and then the ether was distilled. The base produced was dissolved in 30 cm3 of acetone and then a solution of 34 g of hydrochloric acid in 330 cm3 of acetone was added. The hydrochloride precipitate was dried, washed with acetone and then dried. After recrystallization from isopropyl alcohol, 154 g of N-(1-ethyl-2-pyrrolidylmethyl)-2,3-methylenedioxybenzamide hydrochloride was produced (M.P.: 127.5°-128.5° C.; yield: 49.7%).

Workup

  1. additionwere introduced into a balloon flask
  2. customprovided with an agitator
  3. distillationwas distilled
  4. filtrationthe remaining solution was filtered
  5. additionAfter the addition of 120 cm3 of 20% ammonia and extraction with ether
  6. customthe ethereal solution was dried on potassium carbonate
  7. distillationthe ether was distilled
  8. customThe base produced
  9. dry with materialThe hydrochloride precipitate was dried
  10. washwashed with acetone
  11. customdried
  12. customAfter recrystallization from isopropyl alcohol

Sources & evidence

ORD record
ord-b45c1c9d2ee54f2dac5c48160804393b
Source dataset
uspto-grants-1981_05
Patent number
US04268512

Reaction notes

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