1-Methylpiperazine → HCID 12562530, compound

HRID 1973124Notes

Reaction equation

HRID 1973124 reaction equation
Br[C:2]1[N:6]2[C:7]3[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:8]=3[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:10][CH2:11][C:5]2=[N:4][N:3]=1.[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(=O)(O)[O-].[Na+]>O>[Br:22][C:19]1[CH:20]=[CH:21][C:7]2[N:6]3[C:2]([N:27]4[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]4)=[N:3][N:4]=[C:5]3[CH2:11][N:10]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[C:8]=2[CH:18]=1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 12562520HCID 12562520, compound

Product 1

HCID 12562530HCID 12562530, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 1,8-dibromo-6-(2-pyridyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine (2.19 g.) and 1-methylpiperazine (10 ml.) is kept under nitrogen at 125°-130° C. for 15.5 hours and at 135°-145° C. for 24 hours. It is then cooled, mixed with cold water, treated with a little sodium bicarbonate and extracted with chloroform. The extract is washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue is treated successively with xylene and toluene with concentration after each addition and the resulting material is chromatographed on silica gel (150 g.) with mixtures of chloroform and methanol containing 5-10% methanol. The product thus obtained is crystallized from methanol-ethyl acetate to give 8-bromo-1-(4-methylpiperazino)-6-(2-pyridyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine in 4 crops as follows: 0.799 g., melting point 250.5°-253.5° dec; 0.062 g., melting point 248.5-249.5° dec; 0.344 g., melting point 250°-252° dec., and 0.206 g., melting point 245.5°-247.5° dec. The analytical sample has a melting point of 252°-253° dec.

Workup

  1. temperatureIt is then cooled
  2. extractionextracted with chloroform
  3. washThe extract is washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. additionThe residue is treated successively with xylene and toluene with concentration
  7. additionafter each addition
  8. customthe resulting material is chromatographed on silica gel (150 g.) with mixtures of chloroform and methanol containing 5-10% methanol
  9. customThe product thus obtained
  10. customis crystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-f3e49d9f08ca40148d86bbda59596a3d
Source dataset
uspto-grants-1976_12
Patent number
US03996230

Reaction notes

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