Piperidine → Ethyl alpha-phenyl-1-piperidineacetate

HRID 404612Notes

Reaction equation

HRID 404612 reaction equation
CCN(C(C)C)C(C)C.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.Br[CH:17]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(#N)C>[C:23]1([CH:17]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 97780Ethyl bromophenylacetate

Product 1

HCID 202135Ethyl alpha-phenyl-1-piperidineacetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

DIPEA (0.86 ml, 4.94 mmol) and piperidine (0.49 ml, 4.94 mmol) were sequentially added to a solution of ethyl 2-bromo-2-phenylacetate (0.72 ml, 4.11 mmol) in acetonitrile (13 ml). The pale yellow solution was stirred at room temperature monitoring by TLC (petroleum ether/EtOAc=9/1). After 1.5 hours complete conversion into the desired product was detected. Solvent was evaporated and the residue (pale yellow solid) was triturated with Et20 (30 ml). The solid was filtered off and the ethereal solution was evaporated to dryness. The residue was purified by flash chromatography (petroleum ether/EtOAc=95/5) to collect ethyl 2-phenyl-2-(piperidin-1-yl)acetate (990 mg, 97% yield) as a colorless oil.

Sources & evidence

ORD record
ord-67ba5dac437f4cb89a9b16a81c95448b
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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