Hydrochloric Acid → HCID 20400808, compound

HRID 1980877Notes

Reaction equation

HRID 1980877 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[CH3:2].[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1.BrBr.[ClH:25]>O1CCOCC1.CCOCC>[ClH:25].[N:18]1([C:9]2[NH:10][C:11]3[C:16]([C:8]=2[CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:17])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:22]=[CH:21][N:20]=[CH:19]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 24408Bromine2×HCID 292652ethyl 4-(1h-indol-3-yl)butanoate

Product 1

HCID 20400808HCID 20400808, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent3×

Procedure

To a solution of ethyl-4-(3-indolyl)butyrate (3.00 g) and imidazole (4.43 g) in dioxane (75 ml) stirring at 10° is added dropwise while stirring a solution of bromine (0.65 ml) in dioxane (25 ml) over a period of 2.5 hours. Immediately upon the addition of bromine the reaction mixture becomes a thick suspension. Additional dioxane (30 ml) is added to keep the reacton mixture more mobile. Upon complete addition to cooling bath is removed and the reaction mixture allowed to stir at room temperature overnight. The suspended solid is removed by vacuum filtration and the filtrate concentrated in vacuo to give an orange oil. This oil is suspended in either (100 ml) and extracted with 1N hydrochloric acid (1×50 ml). The aqueous layer is washed with ether (1×100 ml), made basic with 3 N sodium hydroxide (12 ml), and extracted with ether (2×100 ml). This ether extract is washed with brine, dried (MgSO4 ), filtered, and concentrated in vacuo to give an orange oil which becomes partially crystalline. This material (1.38 g) is dissolved in 20 ml ether and to the solution is added 0.65 ml of 7.1M ethanolic hydrogen chloride. The salt separates as an oil which crystallizes on addition of a few milliliters of ethanol to yield 2-(1-imidazolyl)-3-(-3-ethoxycarbonylpropyl)indole hydrochloride, m.p. 152°-155°.

Workup

  1. additionis added dropwise
  2. additionUpon complete addition
  3. temperatureto cooling bath
  4. customis removed
  5. customThe suspended solid is removed by vacuum filtration
  6. concentrationthe filtrate concentrated in vacuo
  7. customto give an orange oil
  8. extractionextracted with 1N hydrochloric acid (1×50 ml)
  9. washThe aqueous layer is washed with ether (1×100 ml)
  10. extractionextracted with ether (2×100 ml)
  11. extractionThis ether extract
  12. washis washed with brine
  13. dry with materialdried (MgSO4 )
  14. filtrationfiltered
  15. concentrationconcentrated in vacuo
  16. customto give an orange oil which
  17. customcrystallizes on addition of a few milliliters of ethanol

Sources & evidence

ORD record
ord-83ef2ae0f9a645488af21359594faafd
Source dataset
uspto-grants-1985_04
Patent number
US04511573

Reaction notes

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