1-Methylpiperazine → 4H-Thieno(3,4-b)(1,5)benzodiazepine, 7-chloro-10-(4-methyl-1-piperazinyl)-

HRID 371635Notes

Reaction equation

HRID 371635 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3=[CH:12][S:13][CH:14]=[C:9]3[C:8](SC)=[N:7][C:6]=2[CH:17]=1.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3=[CH:12][S:13][CH:14]=[C:9]3[C:8]([N:22]3[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]3)=[N:7][C:6]=2[CH:17]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 125216627-Chloro-10-(methylthio)-4H-thieno[3,4-b] [1,5]benzodiazepine

Product 1

HCID 30423894H-Thieno(3,4-b)(1,5)benzodiazepine, 7-chloro-10-(4-methyl-1-piperazinyl)-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

A solution of 0.9 g. of 7-chloro-10-(methylthio)-4H-thieno[3,4-b][1,5]benzodiazepine in 4.5 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. The sticky precipitate is collected and dissolved in chloroform. The dried chloroform solution is concentrated under reduced pressure to give 7-chloro-10-(4-methyl-1-piperazinyl)-4H-thieno[3,4-b][1,5]benzodiazepine as an oil. An ethanolic solution of the oil is treated with 70% perchloric acid and diluted with water. The precipitate is recrystallized from methanol to give yellow crystals, m.p. 268°-270° C. (dec.).

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 sticky precipitate is collected
  8. dissolutiondissolved in chloroform
  9. concentrationThe dried chloroform solution is concentrated under reduced pressure

Sources & evidence

ORD record
ord-b849f02c9a784757b7ae752771a944d7
Source dataset
uspto-grants-1978_05
Patent number
US04087421

Reaction notes

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