Potassium Carbonate → 1-{1-[2-(3-Pyridyl)ethyl]piperidin-4-yl}-6-acetamidomethylindole

HRID 1790525Notes

Reaction equation

HRID 1790525 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH2:12][CH2:11][CH:10]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH2:22][NH:23][C:24](=[O:26])[CH3:25])[CH:20]=3)[CH:15]=[CH:14]2)[CH2:9][CH2:8]1.Br[CH2:28][CH2:29][C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1>CN(C)C=O>[N:32]1[CH:33]=[CH:34][CH:35]=[C:30]([CH2:29][CH2:28][N:7]2[CH2:8][CH2:9][CH:10]([N:13]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([CH2:22][NH:23][C:24](=[O:26])[CH3:25])[CH:20]=4)[CH:15]=[CH:14]3)[CH2:11][CH2:12]2)[CH:31]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 111167423-(2-bromoethyl)pyridineHCID 220379271-(Piperidin-4-yl)-6-acetamidomethylindole

Product 1

HCID 220380861-{1-[2-(3-Pyridyl)ethyl]piperidin-4-yl}-6-acetamidomethylindoleYield 75.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (0.5 g) was added to a solution of 1-(piperidin-4-yl)-6-acetamidomethylindole (0.10 g) obtained in Example 386-1) and 3-(2-bromoethyl)pyridine (0.07 g) obtained in Production Example 26-2 in N,N-dimethylformamide (5 ml) and the resultant mixture was stirred at 70° C. for 6 hr. Then the reaction mixtures were concentrated under reduced pressure and the residue was partitioned between ethyl acetate (40 ml) and water (15 ml) followed by extraction with ethyl acetate. The ethyl acetate layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol system) to give the title compound (0.06 g) as a pale yellow wax (yield: 75.5%).

Workup

  1. customThen the reaction mixtures
  2. concentrationwere concentrated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate (40 ml) and water (15 ml)
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe ethyl acetate layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform/methanol system)

Sources & evidence

ORD record
ord-11e78a2fcddc4818bf1574250803ddad
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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