4-Piperidinecarboxamide → HCID 86688908, compound

HRID 404649Notes

Reaction equation

HRID 404649 reaction equation
Br[CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].CCN(C(C)C)C(C)C.[NH:23]1[CH2:28][CH2:27][CH:26]([C:29]([NH2:31])=[O:30])[CH2:25][CH2:24]1>C(#N)C>[C:29]([CH:26]1[CH2:27][CH2:28][N:23]([CH:2]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:24][CH2:25]1)(=[O:30])[NH2:31]

Participants

5

Reactant 3

HCID 37724-PiperidinecarboxamideHCID 81531DiisopropylethylamineHCID 97780Ethyl bromophenylacetate

Product 1

HCID 86688908HCID 86688908, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 2-bromo-2-phenylacetate (0.22 ml, 1.23 mmol) was dissolved in acetonitrile (4 ml). DIPEA (0.28 ml, 1.60 mmol) and piperidine-4-carboxamide (0.21 g, 1.60 mmol) were sequentially added. The reaction was stirred at room temperature overnight. The mixture was evaporated and the residue was purified by flash chromatography (DCM/Acetone=8/2). The solid was triturated with i-Pr2O to obtain ethyl 2-(4-carbamoylpiperidin-1-yl)-2-phenylacetate (239 mg, 66.7% yield) as a pale yellow solid.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was purified by flash chromatography (DCM/Acetone=8/2)
  3. customThe solid was triturated with i-Pr2O

Sources & evidence

ORD record
ord-b9b7c3b125894b39977c5401ced92bb6
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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