Toluene → 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-(2-pyrrolidon-1-yl)methylindole

HRID 1790517Notes

Reaction equation

HRID 1790517 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([CH2:23][NH2:24])[CH:21]=4)[CH:16]=[CH:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:27]1(=[O:31])O[CH2:29][CH2:28]1.[C:32]1(C)C=CC=CC=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([CH2:23][N:24]5[CH2:32][CH2:29][CH2:28][C:27]5=[O:31])[CH:21]=4)[CH:16]=[CH:15]3)[CH2:12][CH2:13]2)=[CH:25][CH:26]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 2365Beta-PropiolactoneHCID 22038390HCID 22038390, compound

Product 1

HCID 220379311-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-(2-pyrrolidon-1-yl)methylindoleYield 45%

Procedure

A mixture of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-aminomethylindole (150 mg) obtained in Example 322-3), propiolactone (30 mg) and toluene (10 ml) was heated under reflux for 2 hr. Then the reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/ethanol system) to give the title compound (150 mg) as an oil. This oil was then crystallized from ethyl acetate by using oxalic acid (32 mg) to give the oxalate (100 mg) of the title compound as a pale yellow amorphous substance (yield: 45%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hr
  3. concentrationThen the reaction solution was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/ethanol system)

Sources & evidence

ORD record
ord-72804b42f5bf48d8ac80aeeca9d0c7a5
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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