Triethylamine → HCID 86734235, compound

HRID 1973111Notes

Reaction equation

HRID 1973111 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:26])=[N:8][C:9]([N:16]([CH2:24][CH3:25])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1Cl)=[O:5])[CH3:2].[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(N(CC)CC)C>C(O)C>[CH2:24]([N:16]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:9]1[N:8]=[C:7]([CH3:26])[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:11]([N:31]2[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]2)[C:10]=1[N+:13]([O-:15])=[O:14])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 68133424HCID 68133424, compound

Product 1

HCID 86734235HCID 86734235, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

37.8 g. of 4-chloro-6-[ethyl(phenylmethyl)amino]-2-methyl-5-nitro-3-pyridinecarboxylic acid ethyl ester (0.1 Mol.), 12 g. of N-methylpiperazine (0.12 Mol.) and 15 g. of triethylamine (0.15 Mol.) are refluxed in 200 ml. of ethanol for three hours. After this time, the solvent is distilled off, the residue is dissolved in 100 ml. of water, made alkaline with potassium hydroxide and extracted three times with 100 ml. portions of ethyl acetate. The extract is dried with calcium chloride, the solvent distilled off and the residual 6-[ethyl(phenylmethyl)amino]-2methyl-4-(4-methyl-1-piperazinyl)-5-nitropyridine-3-carboxylic acid, ethyl ester is used without further purification, yield of crude product: 40 g. (90%).

Workup

  1. distillationAfter this time, the solvent is distilled off
  2. dissolutionthe residue is dissolved in 100 ml
  3. extractionextracted three times with 100 ml
  4. dry with materialThe extract is dried with calcium chloride
  5. distillationthe solvent distilled off
  6. customthe residual 6-[ethyl(phenylmethyl)amino]-2methyl-4-(4-methyl-1-piperazinyl)-5-nitropyridine-3-carboxylic acid, ethyl ester is used without further purification, yield of crude product

Sources & evidence

ORD record
ord-bbf9156f828243da86f443d506f54607
Source dataset
uspto-grants-1976_12
Patent number
US03996233

Reaction notes

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