Piperazine → 4H-Thieno(3,4-b)(1,5)benzodiazepine, 10-(1-piperazinyl)-

HRID 371629Notes

Reaction equation

HRID 371629 reaction equation
CS[C:3]1[C:4]2[C:5](=[CH:14][S:15][CH:16]=2)[NH:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1.[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>C(O)(=O)C>[N:17]1([C:3]2[C:4]3[C:5](=[CH:14][S:15][CH:16]=3)[NH:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[N:9]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1

Participants

5

Reactant 2

HCID 4837PiperazineHCID 12521659HCID 12521659, compound

Product 1

HCID 30423884H-Thieno(3,4-b)(1,5)benzodiazepine, 10-(1-piperazinyl)-

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 176Acetic AcidSolvent

Procedure

A bomb charged with 2.5 g. of 10-(methylthio)-4H-thieno[3,4-b][1,5]benzodiazepine, 8.6 g. of piperazine, and three drops of acetic acid is placed in an oil bath and heated at 155°-160° C. for 4 days. The bomb is then cooled and the contents are dissolved in 2N acetic acid. The solution is filtered and the filtrate is made alkaline with ammonium hydroxide and extracted with chloroform. The extracts are dried, filtered and evaporated to give a yellow solid. Recrystallization from ethanol gives the product as light tan crystals which melt at 228°-231° C. (dec.).

Workup

  1. additionA bomb charged with 2.5 g
  2. temperatureheated at 155°-160° C. for 4 days
  3. temperatureThe bomb is then cooled
  4. filtrationThe solution is filtered
  5. extractionextracted with chloroform
  6. customThe extracts are dried
  7. filtrationfiltered
  8. customevaporated
  9. customto give a yellow solid
  10. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-cc6f6cc5ab9c4ef6986daf09cce11c4c
Source dataset
uspto-grants-1978_05
Patent number
US04087421

Reaction notes

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