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

HRID 1608987Notes

Reaction equation

HRID 1608987 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)OCC.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][CH2:22][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 15233272(+/-)-3-(1-Methyl-4-piperidyl)-5-(1,3-oxazolidin-4-ylmethyl)-1H-indoleYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of the product from step (f) (1.6 g), diethyl carbonate (0.71 g) 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 column using DCM/EtOH/NH4OH (30:8:1) as eluant to give a colourless foam which was crystallised from isopropanol/ether to give the desired product as a colourless crystalline solid (1.1 g), mp 191°-192° C. 1H NMR and microanalysis as for product of Synthetic Example 4.

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 column
  5. customto give a colourless foam which
  6. customwas crystallised from isopropanol/ether

Sources & evidence

ORD record
ord-022b457f6ac142baba02c650bf6be21a
Source dataset
uspto-grants-1995_03
Patent number
US05399574

Reaction notes

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