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

HRID 371633Notes

Reaction equation

HRID 371633 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

5

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 2

HCID 176Acetic AcidCatalystHCID 176Acetic AcidSolvent

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 concentratedto 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. filtrationThe acidic solution is filtered
  4. temperaturecooled
  5. customThe precipitate is collected
  6. washwashed with water
  7. dissolutiondissolved in chloroform
  8. dry with materialThe chloroform solution is dried
  9. concentrationconcentrated to an oil, which
  10. customslowly crystallizes
  11. customRecrystallization from ethanol
  12. customgives yellow crystals, m.p. 83°-85° C.

Sources & evidence

ORD record
ord-2b8e6549e1464b689285b0bd96501659
Source dataset
uspto-grants-1978_05
Patent number
US04087421

Reaction notes

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