Methanol → 4-(4,4-DIMETHYLPIPERIDIN-1-YL)BENZOIC ACID

HRID 1785773Notes

Reaction equation

HRID 1785773 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:7][CH2:6][N:5]([C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.O[Li].O.CO>C1COCC1.O>[CH3:1][C:2]1([CH3:19])[CH2:7][CH2:6][N:5]([C:8]2[CH:18]=[CH:17][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 11651829Ethyl 4-(4,4-dimethylpiperidin-1-yl)benzoate

Product 1

HCID 115359804-(4,4-DIMETHYLPIPERIDIN-1-YL)BENZOIC ACID

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 119B (260 mg, 1.0 mmol) and LiOH.H2O (158 mg, 4.0 mmol) in THF (19 mL), water (5 mL), and methanol (5 mL) was heated to 75° C. for 18 hours, cooled to room temperature, concentrated, and adjusted to pH 3-4 with 1N HCl. The precipitate was collected by filtration, washed with water, and dried under vacuum to provide the desired product. MS(DCI(+)) m/e 234 (M+H)+.

Workup

  1. concentrationconcentrated
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-76a25e26cdbe433d938f18d3285b7033
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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