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

HRID 457783Notes

Reaction equation

HRID 457783 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][C:23]3[CH:27]=[CH:26][S:25][CH:24]=3)[CH:13]=2)[CH2:8][CH2:7]1)=O)C.[OH-].[K+]>C(O)(C)C>[NH: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][C:23]3[CH:27]=[CH:26][S:25][CH:24]=3)[CH:13]=2)[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 694126194-[1-(2-thiophen-3-yl-ethyl)-1H-indol-3-yl]-piperidine-1-carboxylic acid ethyl ester

Product 1

HCID 179643093-piperidin-4-yl-1-(2-thiophen-3-yl-ethyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

To a solution of 12.7 g (0.033 mol) of 4-[1-(2-thiophen-3-yl-ethyl)-1H-indol-3-yl]-piperidine-1-carboxylic acid ethyl ester in 10 mL of iso-propanol, a solution of 22 g of potassium hydroxide in 220 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 toluene and water. The organic layer was dried with sodium sulfate and after filtration, the solvent was removed under reduced pressure affording 9.3 g (90% 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 toluene and water
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationafter filtration
  5. customthe solvent was removed under reduced pressure
  6. customaffording
  7. custom9.3 g (90% of yield) of an oil which

Sources & evidence

ORD record
ord-0d765f841388409cbc61a82bb6e0d7b8
Source dataset
uspto-grants-2007_03
Patent number
US07189741B2

Reaction notes

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