Lithium Hydroxide → HCID 23149054, compound

HRID 880308Notes

Reaction equation

HRID 880308 reaction equation
C[C:2]1[C:11]([C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[Li+].[OH-]>CO.O>[N:14]1([C:12]([C:11]2[CH:2]=[C:3]([CH:8]=[CH:9][CH:10]=2)[C:4]([OH:6])=[O:5])=[O:13])[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 90239200HCID 90239200, compound

Product 1

HCID 23149054HCID 23149054, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl methyl-3-(morpholine-4-carbonyl)benzoate (300 mg, 1.11 mmol) in MeOH (2 mL) and water (2 mL) was added LiOH (100 mg, 2.38 mmol) at 20° C. The mixture was heated to 60° C. for 1 h under N2. The reaction solution was concentrated in vacuo and diluted with water. The pH was adjusted to 4 with 2N HCl and the aqueous layer was extracted with DCM. The organic layer was concentrated to dryness and obtained the title product that was used in the next reaction without further purification (250 mg, Yield 96%). LCMS (m/z): 236.2 (M+1).

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. additiondiluted with water
  3. extractionthe aqueous layer was extracted with DCM
  4. concentrationThe organic layer was concentrated to dryness

Sources & evidence

ORD record
ord-959f8dccdabf4ba7815cd3e854120206
Source dataset
uspto-grants-2015_03
Patent number
US08993555B2

Reaction notes

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