Water → HCID 9824143, compound

HRID 1383297Notes

Reaction equation

HRID 1383297 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]2)[CH2:11][CH2:10]1.Br[CH2:23][CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][N:18]([CH2:23][CH2:24][C:25]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[NH:27][CH:26]=3)[CH2:17]2)[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 769243-(2-Bromoethyl)indoleHCID 9947928HCID 9947928, compound

Product 1

HCID 9824143HCID 9824143, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(2-methoxy-phenyl)-4-piperidin-3-ylmethyl-piperazine (0.5 g, 1.72 mmol) from example 6, 3-(2-bromoethyl)indole (0.38 g, 1 equivalent) and potassium carbonate (0.48 g, 2 equivalents) in acetonitrile (25 mL) were refluxed for 24 hours under a nitrogen atmosphere. Water (100 mL)) was added and the product extracted into ethyl acetate (3×50 mL). The combined organics were washed with water (25 mL), brine (25 mL) and dried over anhydrous sodium sulfate. Filtration and concentration in vacuum afforded the required product. Treatment with excess ethereal HCl gave the hydrochloride salt of the above titled compound as a white solid.

Workup

  1. temperaturewere refluxed for 24 hours under a nitrogen atmosphere
  2. extractionthe product extracted into ethyl acetate (3×50 mL)
  3. washThe combined organics were washed with water (25 mL), brine (25 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationFiltration and concentration in vacuum

Sources & evidence

ORD record
ord-51a6ad85729f40019d211d460de14531
Source dataset
uspto-grants-2001_07
Patent number
US06255302B1

Reaction notes

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