4-Amino-N-[2-(diethylamino)ethyl]-2-methoxybenzamide → Benzo[1,3]-dioxole-5-carboxylic acid [4-(2-diethylamino-ethylcarbarnoyl)-5-methoxy-phenyl]-amide

HRID 32287

Reaction equation

HRID 32287 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[O:7])=[C:4]([O:18][CH3:19])[CH:3]=1.[CH2:20]1[O:31][C:30]2[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][C:22]=2[O:21]1>C(Cl)(Cl)Cl>[CH2:14]([N:11]([CH2:12][CH3:13])[CH2:10][CH2:9][NH:8][C:6]([C:5]1[C:4]([O:18][CH3:19])=[CH:3][C:2]([NH:1][C:25]([C:24]2[CH:28]=[CH:29][C:30]3[O:31][CH2:20][O:21][C:22]=3[CH:23]=2)=[O:26])=[CH:17][CH:16]=1)=[O:7])[CH3:15]

Participants

4

Reactant 2

HCID 773744-Amino-N-[2-(diethylamino)ethyl]-2-methoxybenzamideHCID 27347491,3-Benzodioxole-5-carbonyl chloride

Product 1

HCID 59793341Benzo[1,3]-dioxole-5-carboxylic acid [4-(2-diethylamino-ethylcarbarnoyl)-5-methoxy-phenyl]-amideYield 67%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

200 mg (0.75 mmol) of 4-amino-N-(2-diethylamino-ethyl)-2-methoxy-benzamide in 10 ml of chloroform is mixed with 5 ml of 3,4-methylenedioxybenzoic acid chloride (in chloroform) and this mixture is stirred for 3 hours at room temperature. After concentration by evaporation in a vacuum, the residue is taken up in 40 ml of dilute sodium bicarbonate solution and then extracted with 40 ml of methylene chloride. The methylene chloride phase is washed with water, dried, filtered and concentrated by evaporation. The crude product, 315 mg, is taken up in methylene chloride and purified on silica gel. As a mobile solvent, a mixture that consists of methylene chloride/methanol (97:3→90:10) is used. 210 mg (67% of theory) of benzo[1,3]dioxole-5-carboxylic acid [4-(2-diethylamino-ethylcarbamoyl)-5-methoxy-phenyl]-amide (melting point 131.1° C.) is obtained.

Workup

  1. concentrationAfter concentration
  2. customby evaporation in a vacuum
  3. extractionextracted with 40 ml of methylene chloride
  4. washThe methylene chloride phase is washed with water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation
  8. custompurified on silica gel

Sources & evidence

ORD record
ord-edf55ea1959844a7beb69242da746a76
Source dataset
uspto-grants-2008_09
Patent number
US07427390B2

Linked notes

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