Anthranilamide → Benzamide, 2-((2-(4-(2-phenylethyl)-1-piperazinyl)ethyl)amino)-, monohydrochloride

HRID 1395791Notes

Reaction equation

HRID 1395791 reaction equation
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].Cl.Cl.[CH2:13]([N:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][Cl:29])[CH2:23][CH2:22]1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])(=O)C.[Na+].[NH4+].[OH-]>O>[ClH:29].[CH2:13]([N:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][NH:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([NH2:10])=[O:9])[CH2:23][CH2:22]1)[CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 6942AnthranilamideHCID 14923Ammonium HydroxideHCID 517045Sodium AcetateHCID 70587748HCID 70587748, compound

Product 1

HCID 3050159Benzamide, 2-((2-(4-(2-phenylethyl)-1-piperazinyl)ethyl)amino)-, monohydrochlorideYield 23.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 13.6 g anthranilamide, 34.5 g 4-phenethylpiperazinoethyl chloride dihydrochloride, 17.5 g sodium acetate, and 50 ml water was refluxed for 24 hours, 50 ml water and 50 ml NH4OH was added and the mixture cooled. The liquid was decanted and the oily solid dissolved in 100 ml propanol, 200 ml water added and the solid filtered. The solid was dissolved in 2 liters of dry ether, acidified with dry HCl gas and filtered. The HCl salt was recrystallized from propanol to give 9.2 g product.

Workup

  1. temperaturewas refluxed for 24 hours
  2. temperaturethe mixture cooled
  3. customThe liquid was decanted
  4. dissolutionthe oily solid dissolved in 100 ml propanol
  5. addition200 ml water added
  6. filtrationthe solid filtered
  7. dissolutionThe solid was dissolved in 2 liters of dry ether
  8. filtrationfiltered
  9. customThe HCl salt was recrystallized from propanol

Sources & evidence

ORD record
ord-061f07b86f1248058777f9cd19ee8c00
Source dataset
uspto-grants-1980_05
Patent number
US04205173

Reaction notes

Loading…