Morpholine → Ethyl α-phenyl-4-morpholineacetate

HRID 404633Notes

Reaction equation

HRID 404633 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][O:26][CH2:25][CH2:24]1>C(#N)C>[O: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

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 97780Ethyl bromophenylacetate

Product 1

HCID 600535Ethyl α-phenyl-4-morpholineacetateYield 112.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 2-bromo-2-phenylacetate (0.22 ml, 1.23 mmol) was dissolved in acetonitrile (4.0 ml) and DIPEA (0.26 ml, 1.48 mmol) and morpholine (0.13 ml, 1.481 mmol) were sequentially added. The solution was stirred at room temperature for 1.5 hours. Acetonitrile was evaporated and the residue was purified by flash chromatography (petroleum ether/EtOAc=85/15) to obtain ethyl 2-morpholino-2-phenylacetate (345 mg, quantitative yield) as a colorless oil.

Workup

  1. customAcetonitrile was evaporated
  2. customthe residue was purified by flash chromatography (petroleum ether/EtOAc=85/15)

Sources & evidence

ORD record
ord-e3d60bf2981a40c2924d43e7c6bab509
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

Loading…