Hydrochloric Acid → HCID 67107225, compound

HRID 1623664Notes

Reaction equation

HRID 1623664 reaction equation
[OH-].[Li+].[CH3:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:11]=[CH:12][C:13]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:14]([CH:25]=2)[C:15]([O:17]CC2C=CC=CC=2)=[O:16])[CH2:6][CH2:5]1.Cl>C1COCC1.O.C(OCC)(=O)C>[CH3:3][N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:11]=[CH:12][C:13]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:14]([CH:25]=2)[C:15]([OH:17])=[O:16])[CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67107114HCID 67107114, compound

Product 1

HCID 67107225HCID 67107225, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide (17.25 mg, 0.72 mmol) was added to a stirred solution of phenylmethyl 5-(4-methyl-1-piperazinyl)-2-[(phenylmethyl)oxy]benzoate (may be prepared as described in Description 39; 100 mg, 0.24 mmol) in a mixture of THF:water (3:1, 10 ml). The mixture was heated to reflux for 12 h and then diluted with ethyl acetate (50 ml). 10% aqueous HCl was added to the mixture to adjust the pH to 2. The organic phase was isolated, washed with brine, dried over magnesium sulphate, and concentrated to give a white solid. The product was purified using Comflash to yield the title compound. 50 mg.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 12 h
  3. customThe organic phase was isolated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated
  7. customto give a white solid
  8. customThe product was purified

Sources & evidence

ORD record
ord-acac3bae93484e57ae2bd4f4db2c1991
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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