Water → 2-(4-Bromo-phenyl)-3-(1-methyl-piperidin-4-yl)-propionic acid

HRID 220180Notes

Reaction equation

HRID 220180 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][CH:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)C#N)=[CH:4][CH:3]=1.OS(O)(=O)=O.O.[C:25]([O-:28])([O-])=[O:26].[Na+].[Na+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][CH:12]2[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]2)[C:25]([OH:28])=[O:26])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 592383062-(4-Bromo-phenyl)-3-(1-methyl-piperidin-4-yl)-propionitrile

Product 1

HCID 592383282-(4-Bromo-phenyl)-3-(1-methyl-piperidin-4-yl)-propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The oily residue of 2-(4-bromo-phenyl)-3-(1-methyl-piperidin-4-yl)-propionitrile was hydrolyzed by refluxing for 2 h with 4 mL of concentrated H2SO4 and water (38:28). The mixture was neutralized with Na2CO3, then MeOH (20 mL) was added. The solid was filtered and washed with MeOH (3×10 mL). The combined methanol solution was evaporated to give an oil. MS: calc'd 326 (MH+), exp 326 (MH+).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with MeOH (3×10 mL)
  3. customThe combined methanol solution was evaporated
  4. customto give an oil

Sources & evidence

ORD record
ord-6b9b418d41204654b2aa2995156f50aa
Source dataset
uspto-grants-2012_06
Patent number
US08202866B2

Reaction notes

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