Hydrochloric Acid → 1H-Indole, 3-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-

HRID 847438Notes

Reaction equation

HRID 847438 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:9][CH:8]=[C:7]([CH2:10]O)[C:5]=2[CH:6]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.[Br-].[Li+].[OH-].[K+].Cl.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>C(O)C>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH2:25][CH2:24][N:23]([CH2:10][C:7]2[C:5]3[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=3)[NH:9][CH:8]=2)[CH2:22][CH2:21]1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 13461-(2-Methoxyphenyl)piperazineHCID 3712Indole-3-carbinolHCID 14797Potassium HydroxideHCID 82050Lithium BromideHCID 149026Tetrafluoro-m-phenylenediamine dihydrochloride

Product 1

HCID 28120451H-Indole, 3-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-Yield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

One mole (147 g) of indole-3-carbinol and one mole (192 g) of 1-(2-methoxyphenyl)piperazine were dissolved in 1.5 liters of ethanol 60%. One mole (87 g) of lithium bromide and 0.1 mole (5.6 g) of potassium hydroxide were added, then the reaction medium was heated at reflux under stirring for 24 hours. After the reaction medium had cooled to 60° C., hydrochloric acid was added until persistence of an acidic pH. Then 189 g of the dihydrochloride salt of the title product was allowed to crystallize by cooling at 0° C. overnight, producing a global yield of 59% (m.p. 188°-190° C. with decomposition.)

Workup

  1. temperaturethe reaction medium was heated
  2. temperatureat reflux

Sources & evidence

ORD record
ord-68b9bf8db1914949b05a271879e5cc93
Source dataset
uspto-grants-1992_08
Patent number
US05142052

Reaction notes

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