Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride → HCID 178463888, compound

HRID 72797Notes

Reaction equation

HRID 72797 reaction equation
Cl.C(O[C:5]([CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][C:8]1=O)=[O:6])C.FC(F)(F)C([O-])=O.[CH2:28]([N+:30]([CH2:34][CH3:35])=[C:31]([NH2:33])[NH2:32])[CH3:29].[O-]CC.[Na+]>CCO.O>[CH2:13]([N:10]1[CH2:11][CH2:12][C:7]2[C:5]([OH:6])=[N:33][C:31]([N:30]([CH2:34][CH3:35])[CH2:28][CH3:29])=[N:32][C:8]=2[CH2:9]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 2723880Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochlorideHCID 2723922Sodium ethoxideHCID 131731834Diethyl guanidinium trifluoroacetate

Product 1

HCID 178463888HCID 178463888, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-benzyl-3-oxo-piperidine-4-carboxylic acid ethyl ester hydrochloride (2.11 g, 7.1 mmol) in EtOH (35 mL) was added diethyl guanidinium trifluoroacetate (1.5 g, 7.1 mmol) and sodium ethoxide (21 wt % in EtOH, 6.7 mL). The reaction was heated at reflux for 16 h then cooled to room temperature (rt). The reaction mixture was diluted with H2O and extracted with CH2Cl2 (2×). The combined organic extracts were dried and concentrated. The resulting material was triturated with Et2O to give the title compound (1.54 g, 70%) as a light brown solid. MS (ESI): mass calcd. for C18H24N4O, 312.4; m/z found, 313.3 [M+H]+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 16 h
  3. extractionextracted with CH2Cl2 (2×)
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated
  6. customThe resulting material was triturated with Et2O

Sources & evidence

ORD record
ord-01d0cbeaf12b453bb38a50e5542cd9ac
Source dataset
uspto-grants-2014_09
Patent number
US08829011B2

Reaction notes

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