Hydrochloric Acid → HCID 69038758, compound

HRID 1820818Notes

Reaction equation

HRID 1820818 reaction equation
[CH:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#N)=[CH:7][C:6]=1[C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[CH2:17][CH2:16]1)=[O:14])([CH3:3])[CH3:2].[OH-:31].[Na+].Cl.[OH2:34]>C(O)C>[CH:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]([OH:34])=[O:31])=[CH:7][C:6]=1[C:13]([N:15]1[CH2:16][CH2:17][N:18]([C:21]2[CH:22]=[CH:23][C:24]([C:27]([F:28])([F:30])[F:29])=[CH:25][CH:26]=2)[CH2:19][CH2:20]1)=[O:14])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 69038716HCID 69038716, compound

Product 1

HCID 69038758HCID 69038758, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To 3.2 mmol 4-isopropoxy-3-[4-(4-trifluoromethyl-phenyl)-piperazine-1-carbonyl]-benzonitrile in 15 ml ethanol was added 30 mmol 2 M aq NaOH and the mixture was heated at 85° C. for 16 h. The mixture was then cooled to RT, diluted with water and acidified to pH 1 with conc HCl, and then extracted three times with ethyl acetate. The combined organic phases were dried with Na2SO4, concentrated in vacuo, and the residue purified by chromatography on silica gel (eluant: methanol/dichloromethane 5:95) to afford the title compound. MS (m/e): 435.3 ([M−H]−, 100%)

Workup

  1. temperatureThe mixture was then cooled to RT
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried with Na2SO4
  4. concentrationconcentrated in vacuo
  5. customthe residue purified by chromatography on silica gel (eluant: methanol/dichloromethane 5:95)

Sources & evidence

ORD record
ord-4c6822a011784851a6c3862a0599d914
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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