Hydrochloric Acid → HCID 12806669, compound

HRID 569958Notes

Reaction equation

HRID 569958 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][CH:14]3[O:16][CH2:15]3)=[CH:9][CH:10]=2)[NH:5][C:4](=[O:17])[CH:3]=1.[C:18]1([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O)C.[ClH:33]>CO>[ClH:33].[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][CH:14]([OH:16])[CH2:15][N:27]3[CH2:28][CH2:29][N:24]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:25][CH2:26]3)=[CH:9][CH:10]=2)[NH:5][C:4](=[O:17])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 70961-PhenylpiperazineHCID 14128493HCID 14128493, compound

Product 1

HCID 12806669HCID 12806669, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.4 Grams of 4-methyl-7-(2,3-epoxypropoxy)carbostyril and 1.8 g of 4-phenylpiperazine are mixed with 30 ml of ethanol and heated for 3 hours under refluxing conditions. After cooling the reaction mixture, crystals thus precipitated are collected by filtration and washed with ether. The crude crystals thus obtained are dissolved in 50 ml of methanol and 3 ml of concentrated hydrochloric acid. The mixture then is concentrated under reduced pressure to dryness. The residue thus obtained is recrystallized from ethanol-ether to obtain 2.7 g (yield: 63%) of 4-methyl-7-[2-hydroxy-3-(4-phenylpiperazinyl)propoxy]carbostyril monohydrochloride in the form of colorless crystals with a melting point of 190°-191° C.

Workup

  1. temperatureheated for 3 hours under refluxing conditions
  2. temperatureAfter cooling the reaction mixture, crystals
  3. customthus precipitated
  4. filtrationare collected by filtration
  5. washwashed with ether
  6. customThe crude crystals thus obtained
  7. concentrationThe mixture then is concentrated under reduced pressure to dryness
  8. customThe residue thus obtained
  9. customis recrystallized from ethanol-ether

Sources & evidence

ORD record
ord-ae4ff73f42fc42eaa4e83bd77106acec
Source dataset
uspto-grants-1988_03
Patent number
US04734416

Reaction notes

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