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

HRID 227270Notes

Reaction equation

HRID 227270 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+]>C(O)(C)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 3776IsopropanolSolvent2×

Procedure

To a solution of 16 g (0.054 mol) of 4-[1-(2-ethoxyethyl)-1H-indol-3-yl]-piperidine-1-carboxylic acid ethyl ester in 10 ml of iso-propanol, a solution of 32 g of potassium hydroxide in 270 ml of iso-propanol was added. The crude mixture was refluxed for 16 hours. After cooling at room temperature, the solvent was removed at reduced pressure and the crude mixture was extracted between ethyl acetate and water. The organic layer was dried with sodium sulphate and after filtration, the solvent was removed under reduced pressure affording 9.6 g (71% of yield) of an oil which corresponds to the expected product.

Workup

  1. customthe solvent was removed at reduced pressure
  2. extractionthe crude mixture was extracted between ethyl acetate and water
  3. dry with materialThe organic layer was dried with sodium sulphate
  4. filtrationafter filtration
  5. customthe solvent was removed under reduced pressure
  6. customaffording
  7. custom9.6 g (71% of yield) of an oil which

Sources & evidence

ORD record
ord-1311fc803cca4d688ac1f6168bf9c33f
Source dataset
uspto-grants-2009_07
Patent number
US07560471B2

Reaction notes

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