Ethyl bromoacetate → Methyl 1-(2-ethoxy-2-oxoethyl)-2-(2-phenylethyl)piperidine-4-carboxylate

HRID 383919Notes

Reaction equation

HRID 383919 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]2[CH2:14][CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:12][CH2:11][NH:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C([O-])([O-])=O.[K+].[K+]>C1(C)C(C)=CC=CC=1.CCOC(C)=O>[CH2:24]([O:23][C:21](=[O:22])[CH2:20][N:10]1[CH2:11][CH2:12][CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:14][CH:9]1[CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:25]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 59291561HCID 59291561, compound

Product 1

HCID 54299142Methyl 1-(2-ethoxy-2-oxoethyl)-2-(2-phenylethyl)piperidine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of methyl 2-(2-phenylethyl)piperidine-4-carboxylate in xylene were added ethyl bromoacetate and K2CO3, followed by heating under reflux for 8 hours. The reaction mixture was diluted with EtOAc, the organic layer was washed with water and brine in this order, dried over MgSO4, and then filtered. The filtrate was concentrated under reduced pressure. To the residue was added hexane, and the insolubles were removed by filtration, followed by concentration under reduced pressure. The residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane:EtOAc) to obtain methyl 1-(2-ethoxy-2-oxoethyl)-2-(2-phenylethyl)piperidine-4-carboxylate as a pale brown oil.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 8 hours
  3. washthe organic layer was washed with water and brine in this order
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. additionTo the residue was added hexane
  8. customthe insolubles were removed by filtration
  9. concentrationfollowed by concentration under reduced pressure
  10. customThe residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane:EtOAc)

Sources & evidence

ORD record
ord-c2d176a487ea4fd4a03bf6da8a6fcfff
Source dataset
uspto-grants-2013_02
Patent number
US08367696B2

Reaction notes

Loading…