2-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1) → Ethyl 3-(piperidin-4-yl)benzoate

HRID 1675128Notes

Reaction equation

HRID 1675128 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:3][CH:2]=1.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Pd].C(O)(C)C.O>[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 11356603Ethyl 3-(pyridin-4-yl)benzoate

Product 1

HCID 57880398Ethyl 3-(piperidin-4-yl)benzoateYield 79.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl 3-(pyridin-4-yl)benzoate (1.46 g, 6.42 mmol), 5% palladium on carbon (50% wet) (0.301 g, 0.07 mmol) and citric acid monohydrate (0.601 g, 2.86 mmol) in a mixture of isopropanol (50 mL) and water (5 mL) were stirred under an atmosphere of hydrogen at 20 atmosphere and 70° C. for 15 hours. The reaction was cooled to room temperature, the catalyst removed by filtration and the solvent evaporated to give the crude product, which was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 2M ammonia in methanol to give ethyl 3-(piperidin-4-yl)benzoate (1.190 g, 79%) as a liquid.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthe catalyst removed by filtration
  3. customthe solvent evaporated
  4. customto give the crude product, which
  5. customwas purified by ion exchange chromatography
  6. washThe desired product was eluted from the column

Sources & evidence

ORD record
ord-bfe01b8ce6b64476a77a307b009c478b
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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