Triethylamine → HCID 23323540, compound

HRID 1381196Notes

Reaction equation

HRID 1381196 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]([OH:18])=O)[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH3:36][O:37][C:38]([C:40]1[CH:46]=[CH:45][CH:44]=[CH:43][C:41]=1[NH2:42])=[O:39]>CN(C=O)C>[CH3:36][O:37][C:38]([C:40]1[CH:46]=[CH:45][CH:44]=[CH:43][C:41]=1[NH:42][C:16](=[O:18])[CH2:15][N:12]1[CH2:11][CH2:10][N:9]([C:7](=[O:8])[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:20][CH:19]=2)[CH2:14][CH2:13]1)=[O:39]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8635Methyl AnthranilateHCID 62365Isobutyl chloroformateHCID 20235785[4-(4-Methoxybenzoyl)-1-piperazinyl]acetic acid

Product 1

HCID 23323540HCID 23323540, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2.5 Grams of [4-(4-methoxybenzoyl)-1-piperazinyl]acetic acid was dissolved in 30 ml of DMF, then 1.2 g of triethylamine was added thereto. Under an ice-cooled condition with stirring, 1.4 g of isobutyl chloroformate was added dropwise thereto and stirred for 30 minutes. Then, the reaction mixture was stirred at a room temperature, a DMF solution of 1.6 g of o-methoxycarbonylaniline was added dropwise to the reaction mixture and stirred for 6 hours. The reaction mixture obtained was concentrated to dryness, and the residue obtained was extracted with chloroform and 1 N-sodium hydroxide. The chloroform layer was washed with water, dried and then chloroform was removed by distillation. The residue obtained was crystallized by adding ethyl acetate, the crystals formed were collected by filtration. Recrystallized from ethanol to obtain 2.1 g of o-methoxycarbonyl-α-[4-(4-methoxybenzoyl)-1-piperazinyl]acetanilide in the form of colorless needle-like crystals. Melting point: 167.5°-169.0° C.

Workup

  1. temperatureUnder an ice-cooled condition
  2. stirringstirred for 30 minutes
  3. stirringThen, the reaction mixture was stirred at a room temperature
  4. stirringstirred for 6 hours
  5. customThe reaction mixture obtained
  6. concentrationwas concentrated to dryness
  7. customthe residue obtained
  8. extractionwas extracted with chloroform and 1 N-sodium hydroxide
  9. washThe chloroform layer was washed with water
  10. customdried
  11. customchloroform was removed by distillation
  12. customThe residue obtained
  13. customwas crystallized
  14. additionby adding ethyl acetate
  15. customthe crystals formed
  16. filtrationwere collected by filtration
  17. customRecrystallized from ethanol

Sources & evidence

ORD record
ord-2d34064b05f24288ae67ad4645622c16
Source dataset
uspto-grants-1986_04
Patent number
US04585774

Reaction notes

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