Water → 1-(4-chlorobenzyl)nipecotic acid

HRID 133576Notes

Reaction equation

HRID 133576 reaction equation
O.[Li+].[OH-].[Cl:4][C:5]1[CH:22]=[CH:21][C:8]([CH2:9][N:10]2[CH2:20][CH2:19][CH2:18][CH:12]([C:13]([O:15]CC)=[O:14])[CH2:11]2)=[CH:7][CH:6]=1>C1COCC1>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]2[CH2:20][CH2:19][CH2:18][CH:12]([C:13]([OH:15])=[O:14])[CH2:11]2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 2838484HCID 2838484, compound

Product 1

HCID 35450941-(4-chlorobenzyl)nipecotic acidYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An H2O (25 mL) solution of LiOH (1.66 g) was added to a THF (60 mL) solution of ethyl 1-(4-chlorobenzyl)nipecotate. The resulting reaction mixture was stirred at room temperature for 1.5 hours. The solvent was removed under reduced pressure to provide an amorphous solid. The obtained crude product was purified by column chromatography (SiO2, 50% methanol-dichloromethane) to afford 1-(4-chlorobenzyl)nipecotic acid (9.75 g, 98.2%) as an off-while amorphous solid. The purity was determined by RPLC/MS (>95%). ESI/MS m/e 254.0 (M++H, C13H17ClNO2).

Workup

  1. customThe resulting reaction mixture
  2. customThe solvent was removed under reduced pressure
  3. customto provide an amorphous solid
  4. customThe obtained crude product
  5. customwas purified by column chromatography (SiO2, 50% methanol-dichloromethane)

Sources & evidence

ORD record
ord-c4bb858ba5b04628ba00ba48696a53d8
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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