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

HRID 371648
Notes
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Reaction equation

HRID 371648 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.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C1(C)C(C)=CC=CC=1.[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36]>C(O)(=O)C.C(O)C>[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36].[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[C:4]2=[CH:15][S:16][CH:17]=[C:3]12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 4837PiperazineHCID 7237O-XyleneHCID 444972Fumaric AcidHCID 125216604-Methyl-10-(methylthio)-4H-thieno[3,4-b] [1,5]benzodiazepine

Product 1

HCID 125216894-Methyl-10-(1-piperazinyl)-4H-thieno[3,4-b][1,5]benzodiazepine fumarate

Reagents, catalysts & solvents 2

HCID 176
Acetic Acid
Catalyst
HCID 702EthanolSolvent2×

Procedure

A mixture comprising 2.6 g. of 4-methyl-10-(methylthio)-4H-thieno[3,4-b][1,5]benzodiazepine (U.S. Pat. No. 3,951,981 -- Ex. 7), 8.6 g. of piperazine, 3 drops of acetic acid and 15 ml. of xylene is stirred and refluxed for 4 hours. The reaction mixture is evaporated, washed with water and the residue is dissolved in 50 ml. of 2N acetic acid. The solution is filtered, the filtrate is made alkaline with ammonium hydroxide and extracted with benzene. The extracts are dried over magnesium sulfate, filtered and evaporated producing an amber oil. This oil is dissolved in 20 ml. of ethanol and a mixture of 2.1 g. of fumaric acid in 40 ml. of ethanol is added. The solid is collected and recrystallized from 125 ml. of methanol giving the desired product as the fumarate salt, m.p. 205°-206° C. (dec.).

Workup

  1. temperaturerefluxed for 4 hours
  2. customThe reaction mixture is evaporated
  3. washwashed with water
  4. dissolutionthe residue is dissolved in 50 ml
  5. filtrationThe solution is filtered
  6. extractionextracted with benzene
  7. dry with materialThe extracts are dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customproducing an amber oil
  11. dissolutionThis oil is dissolved in 20 ml
  12. customThe solid is collected
  13. customrecrystallized from 125 ml

Sources & evidence

ORD record
ord-e1d5247890034975b3d50245f834917e
Source dataset
uspto-grants-1978_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04087421

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes