Hydrochloric Acid → HCID 54515007, compound

HRID 1417775Notes

Reaction equation

HRID 1417775 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-91d4d043bcca4a4d9fde4e1f21d3bac3
Source dataset
uspto-grants-1999_03
Patent number
US05877296

Reaction notes

Loading…