Diisopropylethylamine → HCID 86688912, compound

HRID 404653Notes

Reaction equation

HRID 404653 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].[CH3:14][CH:15]1[CH2:20][CH:19]([CH3:21])[CH2:18][NH:17][CH2:16]1.CCN(C(C)C)C(C)C>C(#N)C>[CH3:14][CH:15]1[CH2:20][CH:19]([CH3:21])[CH2:18][N:17]([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])[CH2:16]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 97780Ethyl bromophenylacetateHCID 1182593,5-Dimethylpiperidine

Product 1

HCID 86688912HCID 86688912, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 2-bromo-2-phenylacetate (0.22 ml, 1.23 mmol), 3,5-dimethylpiperidine (0.20 ml, 1.48 mmol), and DIPEA (0.26 ml, 1.48 mmol) were dissolved in acetonitrile (12 ml) and stirred at room temperature for 16 hours. Acetonitrile was evaporated and the crude was purified by flash chromatography (Petroleum ether/EtOAc=95/5) to obtain ethyl 2-(3,5-dimethylpiperidin-1-yl)-2-phenylacetate (203 mg, 59.7% yield) as colourless oil.

Workup

  1. customAcetonitrile was evaporated
  2. customthe crude was purified by flash chromatography (Petroleum ether/EtOAc=95/5)

Sources & evidence

ORD record
ord-228dca9b233c462d962de726c5dae17c
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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