Dimethylformamide → 1-{4-[(1-Hydroxyethyl)phenethyl]-piperidin-4-yl}-6-acetamidomethylindole

HRID 1790526Notes

Reaction equation

HRID 1790526 reaction equation
[C:1](=[O:4])([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.O[CH:28]([C:30]1[CH:38]=[CH:37][C:33](CCBr)=[CH:32][CH:31]=1)[CH3:29].[CH3:39]N(C)C=O>>[OH:4][CH:1]([CH:29]([C:10]1([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][NH:7][CH2:12][CH2:11]1)[CH2:28][C:30]1[CH:38]=[CH:37][CH:33]=[CH:32][CH:31]=1)[CH3:39]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 220379271-(Piperidin-4-yl)-6-acetamidomethylindoleHCID 220379344-(1-Hydroxyethyl)phenethyl bromide

Product 1

HCID 220380321-{4-[(1-Hydroxyethyl)phenethyl]-piperidin-4-yl}-6-acetamidomethylindoleYield 45.3%

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 4-(1-hydroxyethyl)phenethyl bromide (0.07 g) obtained in Production Example 19 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 chloroform (40 ml) and water (15 ml). The chloroform 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 (0.07 g) as a pale yellow wax (yield: 45.3%).

Workup

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

Sources & evidence

ORD record
ord-e15c3dfc89994171b108cb79c4a78f5e
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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