1-Methylpiperazine → 4-Methyl-10-(4-methyl-1-piperazinyl)-4H-thieno[3,4-b][1,5] benzodiazepine

HRID 1605909Notes

Reaction equation

HRID 1605909 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5](SC)[C:4]2=[CH:15][S:16][CH:17]=[C:3]12.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>C(O)(=O)C>[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]([N:22]2[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]2)[C:4]2=[CH:15][S:16][CH:17]=[C:3]12

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 125216604-Methyl-10-(methylthio)-4H-thieno[3,4-b] [1,5]benzodiazepine

Product 1

HCID 30576994-Methyl-10-(4-methyl-1-piperazinyl)-4H-thieno[3,4-b][1,5] benzodiazepine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

A solution of 1.2 g. of 4-methyl-10-(methylthio)-4H-thieno[3,4-b] [1,5] benzodiazepine in 6 ml. of N-methylpiperazine is treated with 2-3 drops of glacial acetic acid and heated under reflux for 4 days. The solution is concentrated to dryness and the residue is warmed with dilute acetic acid. The acidic solution is filtered, cooled, and made alkaline with concentrated ammonium hydroxide solution. The precipitate is collected, washed with water and dissolved in chloroform. The chloroform solution is dried and concentrated to an oil, which slowly crystallizes. Recrystallization from ethanol gives yellow crystals, m.p. 83°-85°C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 days
  3. concentrationThe solution is concentrated to dryness
  4. temperaturethe residue is warmed with dilute acetic acid
  5. filtrationThe acidic solution is filtered
  6. temperaturecooled
  7. customThe precipitate is collected
  8. washwashed with water
  9. dissolutiondissolved in chloroform
  10. dry with materialThe chloroform solution is dried
  11. concentrationconcentrated to an oil, which
  12. customslowly crystallizes
  13. customRecrystallization from ethanol
  14. customgives yellow crystals, m.p. 83°-85°C.

Sources & evidence

ORD record
ord-825cc660ba5c4256852a9eb249c3abf8
Source dataset
uspto-grants-1976_04
Patent number
US03951981

Reaction notes

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