Lithium Hydroxide → 3-[(Morpholin-4-yl)methyl]benzoic acid

HRID 880315Notes

Reaction equation

HRID 880315 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13]C)=[O:12])[CH2:3][CH2:2]1.[Li+].[OH-]>CO.O>[O:1]1[CH2:2][CH2:3][N:4]([CH2:7][C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([OH:13])=[O:12])[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 437850methyl 3-(morpholin-4-ylmethyl)benzoate

Product 1

HCID 71526923-[(Morpholin-4-yl)methyl]benzoic acidYield 42.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 3-(morpholinomethyl)benzoate (150 mg, 0.64 mmol) in MeOH (2 mL) and water (2 mL) was added LiOH (55 mg, 1.31 mmol) at 20° C. The mixture was heated to 60° C. for 1 h. The reaction solution was concentrated and purified via prep-HPLC to give the title compound (60 mg, Yield 42.5%). LCMS (m/z): 222 (M+1).

Workup

  1. concentrationThe reaction solution was concentrated
  2. custompurified via prep-HPLC

Sources & evidence

ORD record
ord-477e84f45fe4441589b6c34a0e28975c
Source dataset
uspto-grants-2015_03
Patent number
US08993555B2

Reaction notes

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