Tetrahydrofuran → HCID 44473058, compound

HRID 1990986Notes

Reaction equation

HRID 1990986 reaction equation
CC1C=CC(S(OC[CH2:13][CH2:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[C:17]([S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])=[CH:18][NH:19]3)(=O)=O)=CC=1.[CH2:33]([NH:35][CH3:36])[CH3:34].[CH2:37]1COCC1>[OH-].[Na+]>[CH2:33]([N:35]([CH3:37])[CH2:36][CH2:13][CH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[C:17]([S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])=[O:25])=[CH:18][NH:19]2)[CH3:34]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 12219N-MethylethylamineHCID 58955105HCID 58955105, compound

Product 1

HCID 44473058HCID 44473058, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 3-[3-(phenylsulfonyl)-1H-indol-4-yl]propyl 4-methylbenzenesulfonate (0.21 g, 0.447 mmol) in anhydrous THF (5 mL) was added N-ethylmethylamine (0.77 mL, 8.944 mmol) and the reaction mixture heated to 65° C. in a sealed vessel for 16 hours. 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 N-ethyl-N-methyl-3-[3-(phenylsulfonyl)-1H-indol-4-yl]propan-1-amine as a cream solid (0.16 g, 100%). The product was dissolved in absolute ethanol (10 mL), 1.25 N HCl in ethanol (0.47 mL, 0.583 mmol, 1.3 equivalents) added, the mixture stirred for 15 min and then concentrated in vacuo to afford a yellow syrup. The product was crystallized from ethanol (5 mL) to give the title compound as white needles (0.121 g, 69%). MS (ES+) m/z 356.9 (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

Sources & evidence

ORD record
ord-8f7ba8776335413c8a2381facc9694c7
Source dataset
uspto-grants-2010_01
Patent number
US07645752B2

Reaction notes

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