Potassium Carbonate → 5-Nitro-2-(2-[4-phenyl-1-piperazinyl]ethylamino)benzoic acid

HRID 1439601Notes

Reaction equation

HRID 1439601 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:19][CH2:18]1.C([O-])([O-])=O.[K+].[K+].C(O)CC(C)C>C(O)CCC>[N+:11]([C:8]1[CH:9]=[CH:10][C:2]([NH:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 172872-Chloro-5-nitrobenzoic acidHCID 31260Isoamyl AlcoholHCID 47425032-(4-Phenylpiperazin-1-yl)ethan-1-amine

Product 1

HCID 203383135-Nitro-2-(2-[4-phenyl-1-piperazinyl]ethylamino)benzoic acidYield 66.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

2-Chloro-5-nitrobenzoic acid (179 g), 182.5 g 1-(2-aminoethyl)-4-phenylpiperazine, 138 g K2CO3, 900 ml isoamyl alcohol and CuO catalyst were refluxed for 8 hours adding a pinch of CuO periodically. The mixture was cooled overnight, diluted with butanol and filtered. The solid was dissolved in water and neutralized to pH 4-4.5 with 3N HCl to give 247 g crude product. This was recrystallized from 3.5 liters dimethylformamide and 1 liter of water to give 220 g product, m.243-6°.

Workup

  1. additionadding a pinch of CuO periodically
  2. temperatureThe mixture was cooled overnight
  3. filtrationfiltered
  4. dissolutionThe solid was dissolved in water and neutralized to pH 4-4.5 with 3N HCl
  5. customto give 247 g crude product
  6. customThis was recrystallized from 3.5 liters dimethylformamide and 1 liter of water

Sources & evidence

ORD record
ord-6080f7ac426a4d37b06d104a33ac3391
Source dataset
uspto-grants-1977_11
Patent number
US04060526

Reaction notes

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