Diethyl Carbonate → (+/-)-3-(1-Methyl-4-piperidyl)-5-(2-oxo-1,3-oxazolidin-4-ylmethyl)-1H-indole

HRID 343899Notes

Reaction equation

HRID 343899 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][CH:18]([NH2:21])[CH2:19][OH:20])[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1.[C:22](=O)(OCC)[O:23]CC.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][CH:18]4[CH2:19][O:20][C:22](=[O:23])[NH:21]4)[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 11430Potassium CarbonateHCID 15233280(+/-)-3-[3-(1-Methyl-4-piperidyl)-1H-indol-5-yl]-2-amino-1-propanol

Product 1

HCID 15233271(+/-)-3-(1-Methyl-4-piperidyl)-5-(2-oxo-1,3-oxazolidin-4-ylmethyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of the product from step (g) (1.6 g), diethyl carbonate (0.73 ml) and potassium carbonate (0.08 g) was heated at 130° C. for 5 hours. The mixture was cooled, taken up in methanol and the insoluble potassium carbonate filtered off. The filtrate was evaporated in vacuo and the residue eluted through a silica colum using DCM/EtOH/NH4OH (30:8:1) as eluant. The eluate was evaporated in vacuo and the residue recrystallised from isopropanol/ether to give the desired product as a colourless crystalline solid (1.1 g), mp 191°-192° C.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe insoluble potassium carbonate filtered off
  3. customThe filtrate was evaporated in vacuo
  4. washthe residue eluted through a silica colum
  5. customThe eluate was evaporated in vacuo
  6. customthe residue recrystallised from isopropanol/ether

Sources & evidence

ORD record
ord-1900916bbb16437cb0ff2b9f01ca141d
Source dataset
uspto-grants-1999_01
Patent number
US05863935

Reaction notes

Loading…