Dimethylformamide → HCID 10019598, compound

HRID 1244798Notes

Reaction equation

HRID 1244798 reaction equation
[OH-].[K+].CN(C=O)C.[CH2:8]([O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[CH:19]2)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Cl)=[CH:28][CH:27]=1>O>[CH2:8]([O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([CH2:30][C:29]1[CH:32]=[CH:33][C:26]([F:25])=[CH:27][CH:28]=1)[CH:20]=[CH:19]2)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 96024-Fluorobenzyl chlorideHCID 146245-BenzyloxyindoleHCID 14797Potassium Hydroxide

Product 1

HCID 10019598HCID 10019598, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
10 °C

Procedure

The KOH pellets are added to the mixture of DMF and water, and the mixture is vigorously stirred for 5 minutes. After addition of the 5-benzyloxyindole, the mixture is stirred at room temperature for a further 45 minutes. Then, at an internal temperature of 10–20° C., 4-fluorobenzyl chloride is added dropwise while stirring. The mixture is then stirred at room temperature for a further 90 minutes. The mixture is cooled to 10° C., and 300 ml of water are added. It is cooled during this so that the internal temperature does not exceed 20° C. The mixture is stirred for 2 hours, and then the precipitate is filtered off with suction, washed with water and dried at 30° C. initially in circulating air and then in vacuo. The resulting product is very pure so that no additional purification operation is necessary.

Workup

  1. stirringthe mixture is stirred at room temperature for a further 45 minutes
  2. stirringwhile stirring
  3. stirringThe mixture is then stirred at room temperature for a further 90 minutes
  4. temperatureIt is cooled during this so that the internal temperature
  5. customdoes not exceed 20° C
  6. stirringThe mixture is stirred for 2 hours
  7. filtrationthe precipitate is filtered off with suction
  8. washwashed with water
  9. customdried at 30° C. initially

Sources & evidence

ORD record
ord-f2501aaf49bc403b9b677288aeb16be1
Source dataset
uspto-grants-2006_10
Patent number
US07122674B2

Reaction notes

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