Hydrochloric Acid → HCID 59750632, compound

HRID 748480Notes

Reaction equation

HRID 748480 reaction equation
C[O:2][C:3](=[O:41])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([CH:18]2[CH2:23][CH2:22][N:21]([C:24]3([CH3:40])[CH2:29][CH2:28][N:27]([C:30](=[O:39])[C:31]4[C:36]([CH3:37])=[CH:35][CH:34]=[CH:33][C:32]=4[CH3:38])[CH2:26][CH2:25]3)[CH2:20][CH2:19]2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.[Li+].[OH-].Cl.C([O-])(O)=O.[Na+]>O.CO>[CH3:38][C:32]1[CH:33]=[CH:34][CH:35]=[C:36]([CH3:37])[C:31]=1[C:30]([N:27]1[CH2:28][CH2:29][C:24]([CH3:40])([N:21]2[CH2:20][CH2:19][CH:18]([N:11]([CH2:10][C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:41])=[O:2])=[CH:9][CH:8]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:23][CH2:22]2)[CH2:25][CH2:26]1)=[O:39]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 516892Sodium BicarbonateHCID 59750623HCID 59750623, compound

Product 1

HCID 59750632HCID 59750632, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-({[1′-(2,6-Dimethyl-benzoyl)-4′-methyl-[1,4′]bipiperidinyl-4-yl]-phenyl-amino}-methyl)-benzoic acid methyl ester (180 mg, 0.325 mmol), methanol (10 ml), water (3 ml) and 33 mmol) was heated under reflux for 2 h. The pH was adjusted LiOH (200 mg to 1 with 2 N HCl and then to pH 7 with NaHCO3. The mixture was extracted with ethyl acetate and dried with Na2SO4. The solvent was evaporated and the residue crystallized from methanol/water to give 4-({[1′-(2,6-Dimethyl-benzoyl)-4′-methyl-[1,4′]bipiperidinyl-4-yl]-phenyl-amino}-methyl)-benzoic acid. MS/ESI 540 [M+H]+

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialdried with Na2SO4
  5. customThe solvent was evaporated
  6. customthe residue crystallized from methanol/water

Sources & evidence

ORD record
ord-e7deec56fafc423f840d22174850b3ea
Source dataset
uspto-grants-2008_07
Patent number
US07399771B2

Reaction notes

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