Hydrochloric Acid → HCID 67693453, compound

HRID 1449741Notes

Reaction equation

HRID 1449741 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][S:10]([NH:13][C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][C:18]([C:23]([O:25]CC)=[O:24])=[CH:17]3)(=[O:12])=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+].Cl>O1CCOCC1.O>[N:1]1([CH2:7][CH2:8][CH2:9][S:10]([NH:13][C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][C:18]([C:23]([OH:25])=[O:24])=[CH:17]3)(=[O:12])=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 67693357HCID 67693357, compound

Product 1

HCID 67693453HCID 67693453, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 5-[(3-(piperadin-1-yl)propyl)sulfonamido]indole-2-carboxylate (PREPARATION 83, 1.63 g) is dissolved in 10 ml of dioxane and 5 ml of water. Then 0.59 g of solid potassium hydroxide pellets are added and the reaction is stirred at 20°-25° for 24 hr. Then 8.91 ml of 1N hydrochloric acid is added after diluting the reaction with 100 ml of water. The mixture is extracted with n-butanol (3×50 ml) and the organic layer is separated and evaporated under reduced pressure to provide the title compound, NMR (300 MHz, d6-DMSO) 7.37, 7.27, 7.00, 6.90, 2.91, 2.25, 1.75, 1.31, (peak at 4.3 ppm obscured by DMSO).

Workup

  1. additionafter diluting
  2. extractionThe mixture is extracted with n-butanol (3×50 ml)
  3. customthe organic layer is separated
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-baa3b593a4f146d1b40f4a6382c0ce97
Source dataset
uspto-grants-1997_02
Patent number
US05599930

Reaction notes

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