Acetic Acid → 3-(4-Chlorophenyl)-2,4-dihydro-2-[3-(4-morpholinyl)-propyl]indeno[1,2-c]pyrazole, hydrochloride

HRID 46477Notes

Reaction equation

HRID 46477 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH:6]=[C:7]2[CH2:15][C:14]34O[CH:13]3[CH:12]=[CH:11][CH:10]=[C:9]4[C:8]2=O)=[CH:4][CH:3]=1.[O:20]1[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][NH:29][NH2:30])[CH2:22][CH2:21]1.C(O)(=O)C.Cl>CCO.CC#N>[ClH:1].[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]2[N:29]([CH2:28][CH2:27][CH2:26][N:23]3[CH2:22][CH2:21][O:20][CH2:25][CH2:24]3)[N:30]=[C:8]3[C:9]4[C:14]([CH2:15][C:7]=23)=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 124839384-(3-Hydrazinylpropyl)morpholineHCID 867366912-(p-Chlorobenzylidene)-1-indanone oxide

Product 1

HCID 1317116533-(4-Chlorophenyl)-2,4-dihydro-2-[3-(4-morpholinyl)-propyl]indeno[1,2-c]pyrazole, hydrochlorideYield 134.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

Interaction of 16.1 g (0.059 mole) of 2-(p-chlorobenzylidene)-1-indanone oxide and 10.0 g (0.063 mole) of 3-morpholinopropylhydrazine in 285 ml of EtOH in the presence of 9.6 ml of glacial acetic acid as described in Example 1 yields 20.2 g of crude base as a yellow-orange viscous syrup. The latter is dissolved in 150 ml of warm MeCN, cooled, and treated with 9.3 ml of 5.5 N alcoholic HCl. After filtering a small amount of solid which has separated, the solution is diluted to 550 ml with ether. On rubbing, the crystalline HCl salt rapidly separates. After cooling overnight, the pale yellow solid weighs 20.1 g (78%); m.p. 174°-177° (s. 80°). Crystallization from 60 ml of MeCN gives 17.1 g of cream-colored material; m.p. 181°-183° (s. 140°). Following recrystallization from 60 ml of MeCN, the nearly colorless product weighs 13.7 g (53%); m.p. 181°-183°.

Workup

  1. customyields 20.2 g of crude base as a yellow-orange viscous syrup
  2. temperaturecooled
  3. filtrationAfter filtering a small amount of solid which
  4. customhas separated
  5. additionthe solution is diluted to 550 ml with ether
  6. temperatureAfter cooling overnight
  7. customm.p. 174°-177° (s. 80°)
  8. customCrystallization from 60 ml of MeCN

Sources & evidence

ORD record
ord-7d1fb1abfd2f431d89eef6cc72719dc3
Source dataset
uspto-grants-1979_11
Patent number
US04173634

Reaction notes

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