1,3-Benzodioxol-5-amine → Methyl 4-[3-[N-(3,4-methylenedioxyphenyl)amino]propoxy]benzoate

HRID 359079Notes

Reaction equation

HRID 359079 reaction equation
[CH2:1]1[O:10][C:9]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=2[O:2]1.Cl[CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]1[O:10][C:9]2[CH:8]=[CH:7][C:5]([NH:6][CH2:12][CH2:13][CH2:14][O:15][C:16]3[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=3)=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 3

HCID 843101,3-Benzodioxol-5-amineHCID 516892Sodium BicarbonateHCID 12389265Methyl 4-(3-chloropropoxy)benzoate

Product 1

HCID 14882821Methyl 4-[3-[N-(3,4-methylenedioxyphenyl)amino]propoxy]benzoateYield 75.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3,4-Methylenedioxyaniline (1.80 g), methyl 4-(3chloropropoxy)benzoate (2.0 g) and sodium bicarbonate (1.47 g) in toluene (20 ml) were heated with stirring under refluxing for 29 hours. The reaction solution was concentrated under reduced pressure, and thereto were added water and an equivalent amount of conc. hydrochloric acid, then, the resulting precipitate was collected by filtration. After washed with water, the precipitate was recrystallized from aqueous methanol to give the desired product (2.17 g). mp. 124°-127° C.

Workup

  1. temperatureunder refluxing for 29 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionwere added water
  4. filtrationan equivalent amount of conc. hydrochloric acid, then, the resulting precipitate was collected by filtration
  5. washAfter washed with water
  6. customthe precipitate was recrystallized from aqueous methanol

Sources & evidence

ORD record
ord-d87afd5a21a143158153228a379058e9
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Reaction notes

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