Potassium Carbonate → HCID 22907274, compound

HRID 1378521Notes

Reaction equation

HRID 1378521 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH:24]1[CH2:26][CH2:25]1.C(=O)([O-])[O-]>C(O)C>[CH:24]1([CH2:23][N:1]2[CH2:6][CH2:5][CH:4]([N:7]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH:9]=[CH:8]3)[CH2:3][CH2:2]2)[CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 19660Carbonate IonHCID 81503Bromomethylcyclopropane2×HCID 140907551-(Piperidin-4-yl)-1H-indole

Product 1

HCID 22907274HCID 22907274, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-N-(piperidin-4-yl)-indole (0.6 g, 3 mmol) in dry ethanol (4 mL) was added anhydrous potassium carbonate (680 mg, 4.9 mmol). After stirring for 15 minutes at ambient temperature, bromomethylcyclopropane (0.29 mL,4.5 mmol) was added. Stirring was continued overnight. An additional amount of carbonate (0.22 g) and bromomethylcyclopropane (0.14 mL) was added. After 3 hours, the reaction mixture was quenched with water and extracted with ethyl acetate (3×). The combined organic phase was washed with water, dried, evaporated, and purified by column chromatography on silica gel eluting with methylene chloride/ethanol (98:2). Evaporation of the eluting solvent gave the title compound as an oil (480 mg, 63% yield).

Workup

  1. stirringStirring
  2. waitwas continued overnight
  3. waitAfter 3 hours
  4. customthe reaction mixture was quenched with water
  5. extractionextracted with ethyl acetate (3×)
  6. washThe combined organic phase was washed with water
  7. customdried
  8. customevaporated
  9. custompurified by column chromatography on silica gel eluting with methylene chloride/ethanol (98:2)
  10. customEvaporation of the eluting solvent

Sources & evidence

ORD record
ord-29b022ac710944b885ff0c4456444258
Source dataset
uspto-grants-1997_09
Patent number
US05668152

Reaction notes

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