Potassium Iodide → HCID 54135875, compound

HRID 1109750Notes

Reaction equation

HRID 1109750 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][C:15]([Cl:19])=[CH:16][CH:17]=3)[N:12]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH:11]=2)[CH2:6][CH2:5]1.Br[CH2:28][CH:29]([O:32][CH3:33])[O:30][CH3:31].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O1CCOCC1>[Cl:19][C:15]1[CH:14]=[C:13]2[C:18]([C:10]([CH:7]3[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][NH:1][C:29]([O:32][CH3:33])([O:30][CH3:31])[CH3:28])[CH2:5][CH2:6]3)=[CH:11][N:12]2[C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 816722-Bromo-1,1-dimethoxyethaneHCID 10339222HCID 10339222, compound

Product 1

HCID 54135875HCID 54135875, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-[1-(2-aminoethyl)-4-piperidyl]-6-chloro-1-(4-fluorophenyl)-1H-indole 7b (11 g) in dioxan (100 ml) were added 2-bromo-1,1-dimethoxyethane (5.6 g), potassium carbonate (5 g) and a potassium iodide crystal. The mixture was refluxed for 16 hours. After cooling inorganic salts were filtered off and dioxan evaporated leaving crude 6-chloro-3-[1-[N-(1,1-dimethoxyethyl)-aminoethyl]-4-piperidyl]-1-(4-fluorophenyl)-1H-indole as an oil. The crude product was purified by column chromatography on silica gel (eluted with ethyl acetate/methanol 1:1). Yield: 6 g as an oil. The thus obtained alkylated aminoderivative (6 g) was dissolved in dichloromethane (100 ml) and 2-propylisocyanate (1.1 g) was added. After refluxing for 2 hours dichloromethane was evaporated and the title compound 16a was purified by column chromatography on silica gel (eluted with ethyl acetate/methanol 1:1). Yield: 4.9 g as an oil.

Workup

  1. temperatureThe mixture was refluxed for 16 hours
  2. temperatureAfter cooling inorganic salts
  3. filtrationwere filtered off
  4. customdioxan evaporated

Sources & evidence

ORD record
ord-be0cc25c6da144babf6ac338af6615f3
Source dataset
uspto-grants-1994_06
Patent number
US05322851

Reaction notes

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