1-Methylpiperazine → HCID 53680343, compound

HRID 1706995Notes

Reaction equation

HRID 1706995 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:9]=[C:8]([CH2:10]I)[N:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[C:19](=[O:27])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[N:6]=1)=[O:4].[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>CO>[CH3:1][O:2][C:3]([C:5]1[N:9]=[C:8]([CH2:10][N:32]2[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]2)[N:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[C:19](=[O:27])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 54482160HCID 54482160, compound

Product 1

HCID 53680343HCID 53680343, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 8.0 g (0.015 mole) of 1-[2-(o-chlorobenzoyl)-4-chlorophenyl]-5-(iodomethyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester [see Example 13 b)] and 3.3 ml of 1-methyl-piperazine in 160 ml of methanol is stirred for 16 hours at 40°. The reaction solution is then concentrated in vacuo; water is added to the residue and extraction is performed twice with methylene chloride. The organic phase is washed twice with icewater, and extraction is then performed twice with 2N hydrochloric acid solution. To the aqueous acidified extracts there are added ice and sufficient 5N sodium hydroxide solution to bring the pH-value to 10. The base that has precipitated is taken up in ether. The organic phase is washed twice with saturated sodium chloride solution; it is afterwards dried over sodium sulphate and concentrated in vacuo to dryness. There is obtained 1-[2-(o-chlorobenzoyl)-4-chlorophenyl]-5-[(4-methyl-1-piperazinyl)-methyl]-1H-1,2,4-triazole-3-carboxylic acid methyl ester as solidified foam.

Workup

  1. concentrationThe reaction solution is then concentrated in vacuo
  2. additionwater is added to the residue and extraction
  3. washThe organic phase is washed twice with icewater, and extraction
  4. additionare added ice and sufficient 5N sodium hydroxide solution
  5. customThe base that has precipitated
  6. washThe organic phase is washed twice with saturated sodium chloride solution
  7. dry with materialit is afterwards dried over sodium sulphate
  8. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-f7d1c0ed6eef41089d4b2b38cd09cf81
Source dataset
uspto-grants-1980_06
Patent number
US04209516

Reaction notes

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