Hydrochloric Acid → HCID 54515007, compound

HRID 964887Notes

Reaction equation

HRID 964887 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22]C)=[O:21])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CO.C(Cl)Cl.Cl>[OH-].[K+]>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH2:14][CH2:15]2)=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226129Dichloromethane methanolHCID 86752380HCID 86752380, compound

Product 1

HCID 54515007HCID 54515007, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

4-(4-Acetylphenyl)-1-piperazinevaleric acid, methyl ester (15.3 mg) is suspended in 0.1 mL of potassium hydroxide solution (33.2 mg/mL). After heating at 100° C. for 150 min, the starting material is completely dissolved and absent by TLC (10% MeOH/CH2Cl2). After acidifying the reaction solution to pH 4 by adding 0.2N HCl, the aqueous solution is extracted with methylene chloride. After evaporation of the organic layer to dryness, the residue is dissolved in methylene chloride and filtered. Evaporation of the organic layer gives 7 mg of 4-(4-acetylphenyl)-1-piperazinevaleric acid as a white solid. 1H-NMR (CDCl3) spectrum is consistent with the assigned structure. MS (FAB) m/e 305 (M+ +H), 327 (M+ +Na), 348 (M+ +2Na-H).

Workup

  1. extractionthe aqueous solution is extracted with methylene chloride
  2. customAfter evaporation of the organic layer to dryness
  3. dissolutionthe residue is dissolved in methylene chloride
  4. filtrationfiltered
  5. customEvaporation of the organic layer

Sources & evidence

ORD record
ord-bff76db79f3f4ad1b4ff9d467296250a
Source dataset
uspto-grants-1998_06
Patent number
US05773001

Reaction notes

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