Hydrochloric Acid → N-(2-diethylaminoethyl)-4-(1,4-dihydroindeno[1,2-c]-pyrazol-3-yl)-benzamide dihydrochloride

HRID 990999Notes

Reaction equation

HRID 990999 reaction equation
[NH:1]1[C:5]2[C:6]3[C:11]([CH2:12][C:4]=2[C:3]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=O)=[CH:15][CH:14]=2)=[N:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3.[CH2:23]([N:25]([CH2:29][CH3:30])[CH2:26][CH2:27][NH2:28])[CH3:24].[ClH:31]>ClCCl.C(O)C>[ClH:31].[ClH:31].[CH2:23]([N:25]([CH2:29][CH3:30])[CH2:26][CH2:27][NH:28][C:17](=[O:19])[C:16]1[CH:21]=[CH:22][C:13]([C:3]2[C:4]3[CH2:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5]=3[NH:1][N:2]=2)=[CH:14][CH:15]=1)[CH3:24]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 60993N,N-DiethylethylenediamineHCID 18415839Methyl 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoate

Product 1

HCID 18416003N-(2-diethylaminoethyl)-4-(1,4-dihydroindeno[1,2-c]-pyrazol-3-yl)-benzamide dihydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzoate (2.2 g, Example 7) and N,N-diethylethylenediamine (7 ml) was boiled under reflux for 5 hours. The mixture was cooled and stood for 16 hours at ambient temperature. Petroleum ether, b.p. 60-80° C. (50 ml) was added and then decanted off to leave a gum which was further treated with petroleum ether as above and the residual gum dissolved in dichloromethane and purified by flash column chromatography on silica using dichloromethane/IMS/triethylamine (25:2:1) as the mobile phase to give a solid which was dissolved in ethanol (70 ml) and then dry hydrogen chloride gas was passed through the solution. The precipated solid was collected by filtration, washed with ethanol and dried to give N-(2-diethylaminoethyl)-4-(1,4-dihydroindeno[1,2-c]-pyrazol-3-yl)- benzamide dihydrochloride, m.p.230° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. temperatureThe mixture was cooled
  3. customdecanted off
  4. customto leave a gum which
  5. custompurified by flash column chromatography on silica
  6. customto give a solid which
  7. filtrationThe precipated solid was collected by filtration
  8. washwashed with ethanol
  9. customdried

Sources & evidence

ORD record
ord-4b4165ae7d94484ba93cfa00b102bb0a
Source dataset
uspto-grants-2002_10
Patent number
US06462036B1

Reaction notes

Loading…