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Hydrochloric Acid → 3-{4-[(2-Diethylaminoethyl)aminomethyl]phenyl}-1,4-dihydroindeno[1,2-c]pyrazole trihydrochloride

HRID 991012
Notes
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Reaction equation

HRID 991012 reaction equation
[CH2:1]([N:3]([CH2:27][CH3:28])[CH2:4][CH2:5][NH:6][C:7](=O)[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15]3[CH2:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:16]=3[NH:17][N:18]=2)=[CH:10][CH:9]=1)[CH3:2].O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[ClH:40]>C(O)C.O.C(OCC)(=O)C>[ClH:40].[ClH:40].[ClH:40].[CH2:27]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][NH:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[C:15]3[CH2:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:16]=3[NH:17][N:18]=2)=[CH:12][CH:13]=1)[CH3:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 18415783N-(2-diethylaminoethyl)-4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 99563333-{4-[(2-Diethylaminoethyl)aminomethyl]phenyl}-1,4-dihydroindeno[1,2-c]pyrazole trihydrochloride

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(2-diethylaminoethyl)-4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzamide (2.75 g, Example 29) and dry tetrahydrofuran (100 ml) was stirred at room temperature under nitrogen and lithium aluminium hydride (3.4 g) was added portionwise. The reaction mixture was then boiled under reflux for about 2.5 hours, then cooled in an ice/water bath. Ethyl acetate (100 ml) and water (100 ml) were added. Then the organic phase was separated off, washed with brine (25 ml), dried, filtered and evaporated to give a yellow oil. The oil was purified by flash column chromatography on silica using ethyl acetate/ ethanol/ triethylamine (7:2:1) as eluant to give a pale yellow gum. The gum was dissolved in warm ethanol (5 ml), hydrochloric acid (conc, 0.6 ml) was added and the solvent then removed under reduced pressure. The gummy solid residue was boiled up with ethanol (10 ml) and cooled in ice. The precipitated solid was collected by filtration, washed with ethanol and dried to give 3-{4-[(2-diethylaminoethyl)aminomethyl]phenyl}-1,4-dihydroindeno[1,2-c]pyrazole trihydrochloride, m.p. 225° C.

Workup

  1. temperatureunder reflux for about 2.5 hours
  2. temperaturecooled in an ice/water bath
  3. customThen the organic phase was separated off
  4. washwashed with brine (25 ml)
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customto give a yellow oil
  9. customThe oil was purified by flash column chromatography on silica
  10. customto give a pale yellow gum
  11. customthe solvent then removed under reduced pressure
  12. temperaturecooled in ice
  13. filtrationThe precipitated solid was collected by filtration
  14. washwashed with ethanol
  15. customdried

Sources & evidence

ORD record
ord-c3a9fc5abe574538b86fa4ba7a8d5d1f
Source dataset
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06462036B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes