Sulfuric Acid → HCID 9889248, compound

HRID 1840966Notes

Reaction equation

HRID 1840966 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:7]1)[CH3:2].Cl[C:22]1[CH:32]=[CH:31][C:25](C(OCC)=O)=[C:24]([O:33][CH2:34][CH3:35])[CH:23]=1.[C:36](=[O:39])([O-])[O-:37].[K+].[K+].[OH-].[Na+].S(=O)(=O)(O)O>CCCC(=O)C.C(O)C.O>[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH:15]2[CH2:16][CH2:17][N:18]([CH2:35][CH2:34][O:33][C:24]3[CH:25]=[CH:31][C:32]([C:36]([OH:37])=[O:39])=[CH:22][CH:23]=3)[CH2:19][CH2:20]2)=[CH:7]1)[CH3:2]

Participants

9

Reactant 5

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 99036001-(2-ethoxyethyl)-3-piperidin-4-yl-1H-indoleHCID 22494013HCID 22494013, compound

Product 1

HCID 9889248HCID 9889248, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 78952-PentanoneSolvent

Procedure

0.5 g (1.84 mmol) of 4-[1-(2-ethoxy-ethyl)-indol-3-yl]-piperidine and 0.55 g (2.4 mmol) of ethyl 4-chloro-ethoxy-benzoate were disolved in 6 mL of 4-methyl-2-butanone and 0.38 g (2.76 mmol) of potassium carbonate were added. The mixture was refluxed for 18 hours and after cooling, water was added, the organic layer separated, washed with water and brine. The solvent was distilled off. The obtained crude was disolved in 3 mL of ethyl alcohol 96% and 2 mL of a 2N aqueous sodium hydroxide solution were added. After stirring at room temperature for 18 hours the mixture was neutralised with a sulphuric acid solution 10%. The formed solid (0.390 g, 65% yield) was collected, washed with water and dried.

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. temperatureafter cooling
  3. customthe organic layer separated
  4. washwashed with water and brine
  5. distillationThe solvent was distilled off
  6. customThe obtained crude

Sources & evidence

ORD record
ord-3b063024194341de8f4f501a0b79c4a3
Source dataset
uspto-grants-2004_01
Patent number
US06683096B2

Reaction notes

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