2-Bromopropane → 1-[1-(1-Methylethyl)-4-piperidinyl]-1H-indole

HRID 2258583Notes

Reaction equation

HRID 2258583 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+].[CH:22](Br)([CH3:24])[CH3:23]>CN(C=O)C>[CH:22]([N: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)([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 140907551-(Piperidin-4-yl)-1H-indole

Product 1

HCID 229072671-[1-(1-Methylethyl)-4-piperidinyl]-1H-indoleYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(piperidin-4-yl)-indole (0.5 g, 2.5 mmol) in dry DMF (3 m) was added anhydrous potassium carbonate (360 mg, 2.6 mmol). After stirring for 15 minutes at ambient temperature, i-propyl bromide (0.84 mL, 9 mmol) was added. The reaction mixture was refluxed for 2 days with stirring, quenched with water, extracted with ethyl acetate (2×), dried, and evaporated. The remaining residue was chromatographed on silica gel eluting with a toluene/acetone gradient (90:10 to 70:30). Evaporation of the eluting solvent gave the title compound as an oil. (220 mg, 36% yield).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 days
  2. stirringwith stirring
  3. customquenched with water
  4. extractionextracted with ethyl acetate (2×)
  5. customdried
  6. customevaporated
  7. customThe remaining residue was chromatographed on silica gel eluting with a toluene/acetone gradient (90:10 to 70:30)
  8. customEvaporation of the eluting solvent

Sources & evidence

ORD record
ord-20ef55cedf2a47c192d0328b06a7e699
Source dataset
uspto-grants-1997_08
Patent number
US05661173

Reaction notes

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