Isopropylamine → HCID 44473059, compound

HRID 1990985Notes

Reaction equation

HRID 1990985 reaction equation
[C:1]1([S:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[CH2:19][CH2:20][CH2:21]Cl)[NH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:23]([NH2:26])([CH3:25])[CH3:24]>O1CCOCC1.[OH-].[Na+]>[CH:23]([NH:26][CH2:21][CH2:20][CH2:19][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:18]=1[C:10]([S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8])=[CH:11][NH:12]2)([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 6363IsopropylamineHCID 58955102HCID 58955102, compound

Product 1

HCID 44473059HCID 44473059, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-phenylsulfonyl-4-(3-chloro-propyl)-1H-indole (0.255 g, 0.76 mmol) in anhydrous dioxane (5 mL) was added isopropylamine (0.65 mL, 7.64 mmol) and the reaction mixture heated to 70° C. in a sealed vessel for 7 days. The cooled reaction mixture was then diluted with 1 N aqueous NaOH (50 mL) and the resulting milky suspension extracted with ethyl acetate (50 mL). The organic phase was separated, washed with water (50 mL) and brine (50 mL), dried (Na2SO4), filtered and concentrated in vacuo to afford a yellow foam. Purification by flash chromatography (0 to 10% ammonia saturated methanol/dichloromethane) afforded N-isopropyl-3-[3-(phenylsulfonyl)-1H-indol-4-yl]propan-1-amine as a yellow foam (0.23 g, 86%). The product was dissolved in absolute ethanol (10 mL), 1.25 N HCl in ethanol (0.78 mL, 0.98 mmol, 1.5 equivalents) added, the mixture stirred for 15 min and then concentrated in vacuo to afford a yellow foam. The product was crystallized from 1:1 v/v ethanol:tert-butyl methyl ether (10 mL) to give the title compound as white crystals (0.172 g, 57%). MS (ES+) m/z 357.3 (M+H).

Workup

  1. customThe cooled reaction mixture
  2. extractionthe resulting milky suspension extracted with ethyl acetate (50 mL)
  3. customThe organic phase was separated
  4. washwashed with water (50 mL) and brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a yellow foam
  9. customPurification by flash chromatography (0 to 10% ammonia saturated methanol/dichloromethane)

Sources & evidence

ORD record
ord-5274b7f44f0643499634cff08b6f1e33
Source dataset
uspto-grants-2010_01
Patent number
US07645752B2

Reaction notes

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