Lithium Hydroxide → 1-(4-chlorobenzyl)nipecotic acid

HRID 2187799Notes

Reaction equation

HRID 2187799 reaction equation
[Li+].[OH-].[Cl:3][C:4]1[CH:21]=[CH:20][C:7]([CH2:8][N:9]2[CH2:19][CH2:18][CH2:17][CH:11]([C:12]([O:14]CC)=[O:13])[CH2:10]2)=[CH:6][CH:5]=1>O.C1COCC1.CO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[CH2:19][CH2:18][CH2:17][CH:11]([C:12]([OH:14])=[O:13])[CH2:10]2)=[CH:20][CH:21]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 2838484HCID 2838484, compound

Product 1

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

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiOH (1.66 g) in H2O (25 mL) was added to the solution of ethyl 1-(4-chlorobenzyl)nipecotate in THF (60 mL) and CH3OH (20 mL). The reaction mixture was stirred at room temperature for 15 h. The solvent was removed under reduced pressure to afford an amorphous solid which was purified by column chromatography (SiO2, 50% CH3OH—CH2Cl2) to yield-1-(4-chlorobenzyl)nipecotic acid (9.75 g, 98.2%) as a pale yellow amorphous solid. The purity was determined by RPLC/MS (>95%); ESI/MS m/e 254.0 (M++H, C13H17ClNO2).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto afford an amorphous solid which
  3. customwas purified by column chromatography (SiO2, 50% CH3OH—CH2Cl2)

Sources & evidence

ORD record
ord-bdcbb80281ee4f36a8bba56bb938a925
Source dataset
uspto-grants-2002_06
Patent number
US06410566B1

Reaction notes

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