Hydrochloric Acid → 5-[2-(Ethylsulphonyl)ethyl]-3-(1-methyl-4-piperidinyl)-1H-indole hydrochloride

HRID 359454Notes

Reaction equation

HRID 359454 reaction equation
[CH2:1]([S:3](/[CH:6]=[CH:7]/[C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1)(=[O:5])=[O:4])[CH3:2].[ClH:24].O.[H][H]>C(O)C.[Pd]>[ClH:24].[CH2:1]([S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH:17]1[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH2:22]1)(=[O:5])=[O:4])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 15745345(E)-5-[2-(Ethylsulphonyl)ethenyl]-3-(1-methyl-4-piperidinyl)-1H-indoleHCID 178418361HCID 178418361, compound

Product 1

HCID 200650225-[2-(Ethylsulphonyl)ethyl]-3-(1-methyl-4-piperidinyl)-1H-indole hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the product of stage (i) (280 mg) in a mixture of ethanol (40 ml), 2N hydrochloric acid (0.7 ml) and water (5 ml; added to dissolve some precipitated hydrochloride of the starting material) was hydrogenated at room temperature and atmospheric pressure, using 10% palladium on carbon (50% w/w with H2O, 330 mg) as the catalyst. After 1 h; when 22 ml (0.92 mmol) of hydrogen had been absorbed, the reaction was stopped. The mixture was filtered and the filtrate was evaporated to give a foam (302 mg). The foam was crystallised from ethanol (ca. 3 ml) to give the title compound (196 mg) as a powder, with m.p. 229°-232°.

Workup

  1. additionadded
  2. customwas hydrogenated at room temperature
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-1106eca21ef945cb85f2090525358067
Source dataset
uspto-grants-1991_03
Patent number
US05001135

Reaction notes

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