1,3-Benzodioxole-5-carboxylic acid → 1,3-Benzodioxole-5-carboxamide, N-((4-(2-(1-pyrrolidinyl)ethoxy)phenyl)methyl)-

HRID 703529

Reaction equation

HRID 703529 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:16]=[CH:15][C:12]([CH2:13][NH2:14])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:17]1[O:28][C:27]2[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][C:19]=2[O:18]1.C(O)(=O)C1C=CC2OCOC=2C=1.S(Cl)(Cl)=O>C(Cl)(Cl)Cl>[CH2:17]1[O:28][C:27]2[CH:26]=[CH:25][C:21]([C:22]([NH:14][CH2:13][C:12]3[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][N:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)=[CH:16][CH:15]=3)=[O:23])=[CH:20][C:19]=2[O:18]1

Participants

6

Reactant 4

HCID 71961,3-Benzodioxole-5-carboxylic acidHCID 24386Thionyl ChlorideHCID 27347491,3-Benzodioxole-5-carbonyl chlorideHCID 14425929(4-(2-(Pyrrolidin-1-yl)ethoxy)phenyl)methanamine

Product 1

HCID 30788161,3-Benzodioxole-5-carboxamide, N-((4-(2-(1-pyrrolidinyl)ethoxy)phenyl)methyl)-Yield 89.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a cooled solution of 20.0 g of 4-[2-(1-pyrrolidinyl)ethoxy]benzylamine in 30 ml of chloroform was added 17.7 g of 3,4-methylenedioxybenzoyl chloride (which was prepared with 15.9 g of piperonylic acid and 65.3 g of thionyl chloride in the usual manner). The mixture was stirred at room temperature for 20 minutes and the solvent was evaporated. 150 ml of water was added to the residue and the mixture was washed with ethyl acetate. The aqueous layer was made alkaline with potassium carbonate and was extracted with ethyl acetate. The extract was washed with water, dried, and evaporated. The residue was washed with isopropyl ether to give 30.0 g of colorless crystals, which were recrystallized from ethyl acetate as colorless needles, m.p. 93.5°-94.5° C.

Workup

  1. customthe solvent was evaporated
  2. addition150 ml of water was added to the residue
  3. washthe mixture was washed with ethyl acetate
  4. extractionwas extracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. customevaporated
  8. washThe residue was washed with isopropyl ether

Sources & evidence

ORD record
ord-bc3aa1fa71ee41219775f90b89013820
Source dataset
uspto-grants-1991_01
Patent number
US04983633

Linked notes

Loading…