Hydrochloric Acid → HCID 20197235, compound

HRID 652417Notes

Reaction equation

HRID 652417 reaction equation
[ClH:1].[CH3:2][CH:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16]C)=[O:15])=[CH:10][CH:9]=2)[N:6]([CH2:18][CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][N:24]([C:27]3[CH:32]=[C:31]([CH3:33])[CH:30]=[CH:29][N:28]=3)[CH2:23][CH2:22]2)[C:5](=[O:34])[CH2:4]1.CC1N(C2C=CC(C(OC)=O)=CC=2)NC(=O)C1.[OH-].[K+].Cl>C(O)C>[ClH:1].[ClH:1].[CH3:2][CH:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)[N:6]([CH2:18][CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][N:24]([C:27]3[CH:32]=[C:31]([CH3:33])[CH:30]=[CH:29][N:28]=3)[CH2:25][CH2:26]2)[C:5](=[O:34])[CH2:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 20197230HCID 20197230, compoundHCID 70433974HCID 70433974, compound

Product 1

HCID 20197235HCID 20197235, compoundYield 109.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

11 g 5-methyl-1-(4-methoxycarbonylphenyl)-2-{3-[4-(4-methyl-pyrid-2-yl)-piperazin-1-yl]-propyl}-pyrazolin-3-one hydrochloride (see Example No. 48 infra, produced in an analogous manner to Example 2A and B starting from 5-methyl-1-(4-methoxycarbonylphenyl) pyrazolin-3-one) are dissolved in 100 ml 85% ethanol, and the solution is mixed with 5 g potassium hydroxide with stirring at ambient temperature. After completion of the reaction, the reaction mixture is neutralized by the addition of pure hydrochloric acid, and the ethanol is distilled off. The remaining aqueous solution is acidified to a pH of 2 with hydrogen chloride, then the water is distilled off and the residue is dissolved in ethanol. The precipitated mineral salts are removed by suction filtration, and the filtrate is cooled, whereupon the dihydrochloride of the title compound crystallizes out. 6.3 g 5-methyl-1-(4-carboxyphenyl)-2-{3-[4-(4-methyl-pyrid-2-yl)-piperazin-1-yl]-propyl}-pyrazolin-3-one dihydrochloride are obtained, melting point: 205°-225° C.

Workup

  1. custom48 infra, produced in an analogous manner to Example 2A and B
  2. customAfter completion of the reaction
  3. distillationthe ethanol is distilled off
  4. distillationthe water is distilled off
  5. dissolutionthe residue is dissolved in ethanol
  6. customThe precipitated mineral salts are removed by suction filtration
  7. temperaturethe filtrate is cooled, whereupon the dihydrochloride of the title compound
  8. customcrystallizes out

Sources & evidence

ORD record
ord-d989a926f2814715a084345991bcde68
Source dataset
uspto-grants-1987_06
Patent number
US04672063

Reaction notes

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