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O-Xylene → 4-(4-Methyl-4H-thieno[3,4-b][1,5]benzodiazepin-10-yl)-1-piperazineethanol hemifumarate

HRID 371649
Notes
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Reaction equation

HRID 371649 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.[OH:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C1(C)C(C)=CC=CC=1.[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]/[C:38]([OH:40])=[O:39]>C(O)(=O)C.C(O)C>[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]/[C:38]([OH:40])=[O:39].[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]([N:24]2[CH2:25][CH2:26][N:21]([CH2:20][CH2:19][OH:18])[CH2:22][CH2:23]2)[C:4]2=[CH:15][S:16][CH:17]=[C:3]12.[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]([N:24]2[CH2:25][CH2:26][N:21]([CH2:20][CH2:19][OH:18])[CH2:22][CH2:23]2)[C:4]2=[CH:15][S:16][CH:17]=[C:3]12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 7237O-XyleneHCID 76771-(2-Hydroxyethyl)piperazineHCID 444972Fumaric AcidHCID 125216604-Methyl-10-(methylthio)-4H-thieno[3,4-b] [1,5]benzodiazepine

Product 1

HCID 1317110914-(4-Methyl-4H-thieno[3,4-b][1,5]benzodiazepin-10-yl)-1-piperazineethanol hemifumarate

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), 2.6 g. of hydroxyethylpiperazine, 3 drops of acetic acid and 15 ml. of xylene is stirred and refluxed overnight. The mixture is evaporated, washed with water and the residue dissolved in 50 ml. of 2N acetic acid. The solution is filtered. The filtrate is made alkaline with ammonium hydroxide and extracted with chloroform. The extract is dried over magnesium sulfate, filtered and evaporated giving a dark colored oil. This oil is dissolved in 20 ml. of ethanol. A mixture of 1.2 g. of fumaric acid in 25 ml. of ethanol is added and on standing a yellow solid separates. This solid is recrystallized from 75 ml. of ethanol giving the desired product, m.p. 192°-193° C. as the fumarate salt.

Workup

  1. temperaturerefluxed overnight
  2. customThe mixture is evaporated
  3. washwashed with water
  4. dissolutionthe residue dissolved in 50 ml
  5. filtrationThe solution is filtered
  6. extractionextracted with chloroform
  7. dry with materialThe extract is dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customgiving a dark colored oil
  11. dissolutionThis oil is dissolved in 20 ml
  12. additionA mixture of 1.2 g
  13. customThis solid is recrystallized from 75 ml

Sources & evidence

ORD record
ord-39594b6f68b741b3b69f8228051e5735
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