Benzenepropanoic acid → 1-(3-Phenyl-propionyl)-piperidine-4-carboxylic acid benzyl ester

HRID 1177874Notes

Reaction equation

HRID 1177874 reaction equation
CCN(C(C)C)C(C)C.[C:10]1([CH2:16][CH2:17][C:18]([OH:20])=O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH2:42]([O:49][C:50]([CH:52]1[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]1)=[O:51])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CN(C=O)C.O>[CH2:42]([O:49][C:50]([CH:52]1[CH2:57][CH2:56][N:55]([C:18](=[O:20])[CH2:17][CH2:16][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:54][CH2:53]1)=[O:51])[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

8

Reactant 5

HCID 107Benzenepropanoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 114133364-Piperidinecarboxylic acid, phenylmethyl ester

Product 1

HCID 595596251-(3-Phenyl-propionyl)-piperidine-4-carboxylic acid benzyl esterYield 41.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (7 g, 9.44 mL, 54.6 mmol) was added to a stirred solution of 3-phenyl-propionic acid (3.27 g, 21.8 mmol) in DMF (15 mL). HOBT (2.94 g, 21.8 mmol) and EDCI (4.16 g, 21.8 mmol) were then added at room temperature. After 2 minutes, piperidine-4-carboxylic acid benzyl ester (4 g, 18.2 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to get the residue. The obtained residue was purified by column chromatography (using 60-120 silica gel and EtOAc in hexane as eluent) to afford 2.64 g (41.25% yield) of 1-(3-phenyl-propionyl)-piperidine-4-carboxylic acid benzyl ester. LCMS Purity: 86.15%.

Workup

  1. extractionthe product was extracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get the residue
  6. customThe obtained residue was purified by column chromatography (using 60-120 silica gel and EtOAc in hexane as eluent)

Sources & evidence

ORD record
ord-50ac01976b4240d3bb12aecb60167aba
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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