Potassium Hydroxide → 1-(2-ethoxyethyl)-3-piperidin-4-yl-1H-indole

HRID 1840965Notes

Reaction equation

HRID 1840965 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][CH2:22][O:23][CH2:24][CH3:25])[CH:13]=2)[CH2:8][CH2:7]1)=O)C.[OH-].[K+]>CC(O)C>[CH2:24]([O:23][CH2:22][CH2:21][N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]([CH:9]2[CH2:8][CH2:7][NH:6][CH2:11][CH2:10]2)=[CH:13]1)[CH3:25]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 114734154-[1-(2-ethoxyethyl)-1H-indol-3-yl]-piperidine-1-carboxylic acid ethyl ester

Product 1

HCID 99036001-(2-ethoxyethyl)-3-piperidin-4-yl-1H-indole

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
97.5 °C

Procedure

4 g of 4-[1-(2-ethoxy-ethyl)-1H-indol-3-yl]-piperidine-1-carboxylic acid ethyl ester and 3.81 g of potassium hydroxide 85% were added to 14 g of 2-propanol and the mixture was heated at 95-100° C. for 16 hours. The solvent was distilled off and water was added. The mixture was extracted with toluene and the organic layer was separated, washed with water and concentrated. The residue was disolved in a mixture of 10 mL of ethyl alcohol 96% and 6 mL of 2-propanol and 1.4 g of fumaric acid were added. The mixture was refluxed for 30 minutes. After cooling at 0-5° C. for 30 minutes the formed solid was isolated by suction filtration. 4.05 g of a white solid were recovered as a salt of the product with fumaric acid.

Workup

  1. distillationThe solvent was distilled off
  2. additionwater was added
  3. extractionThe mixture was extracted with toluene
  4. customthe organic layer was separated
  5. washwashed with water
  6. concentrationconcentrated
  7. additionThe residue was disolved in a mixture of 10 mL of ethyl alcohol 96% and 6 mL of 2-propanol and 1.4 g of fumaric acid
  8. additionwere added
  9. temperatureThe mixture was refluxed for 30 minutes
  10. temperatureAfter cooling at 0-5° C. for 30 minutes the formed solid
  11. customwas isolated by suction filtration
  12. custom4.05 g of a white solid were recovered as a salt of the product with fumaric acid

Sources & evidence

ORD record
ord-25babfb9b04545b096e8eaa557594dfd
Source dataset
uspto-grants-2004_01
Patent number
US06683096B2

Reaction notes

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