Veratric Acid → o-Methoxycarbonyl--[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide

HRID 1381192Notes

Reaction equation

HRID 1381192 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH3:29][O:30][C:31]([C:33]1[CH:48]=[CH:47][CH:46]=[CH:45][C:34]=1[NH:35][C:36](=[O:44])[CH2:37][N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)=[O:32]>CN(C)C=O>[CH3:29][O:30][C:31]([C:33]1[CH:48]=[CH:47][CH:46]=[CH:45][C:34]=1[NH:35][C:36](=[O:44])[CH2:37][N:38]1[CH2:43][CH2:42][N:41]([C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:40][CH2:39]1)=[O:32]

Participants

6

Reactant 4

HCID 7121Veratric AcidHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 13117362o-Methoxycarbonyl-alpha-(1-piperazinyl)acetanilide

Product 1

HCID 13117363o-Methoxycarbonyl--[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3.3 Grams of 3,4-dimethoxybenzoic acid was dissolved in 30 ml of dimethylformamide, then 2.4 g of triethylamine was added to this solution. Under ice-cooled condition, to this solution was added dropwise 2.75 g of isobutyl chloroformate with stirring, and further stirred for 30 minutes. Then to this reaction mixture was added dropwise a DMF solution containing 5.8 g of o-methoxycarbonyl-α-(1-piperazinyl)acetanilide and stirred for 5 hours. The reaction mixture was concentrated to dryness and subjected to extraction by adding chloroform and 1 N-sodium hydroxide. The chloroform layer was washed with water, dried and removed by distillation, the residue obtained was crystallized by adding ethyl acetate and the crystals formed were collected by filtration. Recrystallized from ethanol to obtain 2.3 g of o-methoxycarbonyl-α-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]acetanilide in the form of colorless needle-like crystals. Melting point: 167.5°-169.0° C.

Workup

  1. temperatureUnder ice-cooled condition
  2. stirringfurther stirred for 30 minutes
  3. stirringstirred for 5 hours
  4. concentrationThe reaction mixture was concentrated to dryness
  5. extractionsubjected to extraction
  6. additionby adding chloroform and 1 N-sodium hydroxide
  7. washThe chloroform layer was washed with water
  8. customdried
  9. customremoved by distillation
  10. customthe residue obtained
  11. customwas crystallized
  12. additionby adding ethyl acetate
  13. customthe crystals formed
  14. filtrationwere collected by filtration
  15. customRecrystallized from ethanol

Sources & evidence

ORD record
ord-ad1ad99e703244eea37960bee29458b2
Source dataset
uspto-grants-1986_04
Patent number
US04585774

Reaction notes

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