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Formaldehyde → 5,11-Dihydro-11-[1-oxo-2-methyl-6-(4-methyl-1-piperazinyl)-4-hexynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

HRID 4175
Notes
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Reaction equation

HRID 4175 reaction equation
[O:1]=[C:2]([N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12](=[O:19])[NH:11][C:10]2[CH:20]=[CH:21][CH:22]=[N:23][C:9]1=2)[CH:3]([CH3:7])[CH2:4][C:5]#[CH:6].C=O.[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.[C:33](O)(=O)/C=C\C(O)=O>O.[Cu]Cl.O1CCOCC1>[O:1]=[C:2]([N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12](=[O:19])[NH:11][C:10]2[CH:20]=[CH:21][CH:22]=[N:23][C:9]1=2)[CH:3]([CH3:7])[CH2:4][C:5]#[C:6][CH2:26][N:27]1[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 531671-MethylpiperazineHCID 444266Maleic AcidHCID 137292075,11-Dihydro-11-[1-oxo-2-methyl-4-pentynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Product 1

HCID 139243965,11-Dihydro-11-[1-oxo-2-methyl-6-(4-methyl-1-piperazinyl)-4-hexynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A reaction mixture consisting of 36.6 g (0.12 mol) of 5,11-dihydro-11-[1-oxo-2-methyl-4-pentynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, 4 g (0.13 mol) of paraformaldehyde, 13.2 g (0.13 mol) of N-methylpiperazine, 0.2 g of copper(I) chloride and 600 ml of dioxan is refluxed for 2 hours. After the reaction has ended the mixture is filtered over activated charcoal to remove the insoluble components and the filtrate is evaporated to dryness in vacuo. In order to purify it, the crude product is suspended in a solution of 15.4 g (0.13 mol) of maleic acid in 600 ml of water and stirred for 1 hour at ambient temperature. The insoluble matter is filtered off, the filtrate is made alkaline by the addition of potassium carbonate and the resin precipitated is taken up in 600 ml of methylene chloride. After drying over magnesium sulphate, the solution is evaporated to dryness in vacuo. The crystalline residue is decocted with 150 ml of ethyl acetate and suction filtered after cooling. By digesting it in a little ethyl acetate a crystalline product is obtained which melts at 212° to 214° C. after washing with ether.

Workup

  1. temperatureis refluxed for 2 hours
  2. filtrationis filtered over activated charcoal
  3. customto remove the insoluble components
  4. customthe filtrate is evaporated to dryness in vacuo
  5. customIn order to purify it
  6. filtrationThe insoluble matter is filtered off
  7. additionby the addition of potassium carbonate
  8. customthe resin precipitated
  9. dry with materialAfter drying over magnesium sulphate
  10. customthe solution is evaporated to dryness in vacuo
  11. filtrationfiltered
  12. temperatureafter cooling
  13. customis obtained which melts at 212° to 214° C.
  14. washafter washing with ether

Sources & evidence

ORD record
ord-6577de97230742bfbdfb63b5e64d45dc
Source dataset
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04724236

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes