2-Morpholinoethylamine → N-(2-morpholinoethyl)-4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzamide monohydrate

HRID 991006Notes

Reaction equation

HRID 991006 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](OC)=[O:18])=[CH:15][CH:14]=2)=[N:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3.[NH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>ClCCl>[OH2:18].[O:29]1[CH2:30][CH2:31][N:26]([CH2:25][CH2:24][NH:23][C:17](=[O:18])[C:16]2[CH:15]=[CH:14][C:13]([C:3]3[C:4]4[CH2:12][C:11]5[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=5)[C:5]=4[NH:1][N:2]=3)=[CH:22][CH:21]=2)[CH2:27][CH2:28]1

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 18415839Methyl 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoate

Product 1

HCID 18415770N-(2-morpholinoethyl)-4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzamide monohydrate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of methyl 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoate (100 mg) and N-(2-aminoethyl)morpholine (0.5 ml) was stirred and heated at 150° C. for 5 hours. The mixture was cooled and washed with petroleum ether, b.p. 40-60° C. (20 ml). The mixture was dissolved in a mixture of dichloromethane/IMS/triethyl-amine (25:2:1) and purified by flash column chromatography on silica using the same solvent mixture as the mobile phase. Appropriate fractions were collected, combined and evaporated to give a gum which was dissolved in dichloromethane, washed with water, then dried, filtered and evaporated to give a solid which was triturated with ether and filtered to give N-(2-morpholinoethyl)-4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzamide monohydrate, m.p. 210-214° C.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with petroleum ether, b.p. 40-60° C. (20 ml)
  3. dissolutionThe mixture was dissolved in a mixture of dichloromethane/IMS/triethyl-amine (25:2:1)
  4. custompurified by flash column chromatography on silica using the same solvent mixture as the mobile phase
  5. customAppropriate fractions were collected
  6. customevaporated
  7. customto give a gum which
  8. washwashed with water
  9. customdried
  10. filtrationfiltered
  11. customevaporated
  12. customto give a solid which
  13. customwas triturated with ether
  14. filtrationfiltered

Sources & evidence

ORD record
ord-7bc3dc14e3214b64b003f08baa66ee9d
Source dataset
uspto-grants-2002_10
Patent number
US06462036B1

Reaction notes

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