Potassium Iodide → 3-(1H-indol-2-yl)propan-1-amine
Reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([NH:9][CH2:10][CH3:11])[CH3:8].[I-].[K+].C(O[CH2:18][CH3:19])(=O)C.[CH3:20]O.C([N:24]([CH2:27][CH3:28])CC)C.[C:29](#N)[CH3:30]>>[NH:9]1[C:10]2[C:29](=[CH:30][CH:18]=[CH:19][CH:11]=2)[CH:8]=[C:7]1[CH2:20][CH2:28][CH2:27][NH2:24]Participants
Procedure
The crude mesylate ester (0.168 g, 0.430 mmol, 1 eq) was suspended in dry acetonitrile (5 mL) under Ar. Potassium carbonate (0.110 g, 0.8 mmol, 2.0 eq) was added followed by the addition of diethylamine (0.083 mL, 0.8 mmol, 2.0 eq) and catalytic potassium iodide. The reaction mixture was stirred and heated to reflux. The reaction was followed by TLC (ethyl acetate/methanol/triethylamine 87/10/3). After 18 hours, the reaction was quenched with aqueous sodium bicarbonate and extracted with ethyl acetate (3×). The combined organic extracts were washed with brine and dried over Na2SO4. After removing the solvent, the residue was loaded on silica gel and chromatographed, eluting with ethyl acetate/methanol/triethylamine 87/10/3. 0.040 g (40% yield) of the indole-propylamine was obtained as a white solid, and converted to the .HCl salt: LC/MS (ESI+) 380 (M+1), Anal. (C24H30N2O2.HCl.0.7H2O) C, H, N.
Workup
- temperatureheated to reflux
- customthe reaction was quenched with aqueous sodium bicarbonate
- extractionextracted with ethyl acetate (3×)
- washThe combined organic extracts were washed with brine
- dry with materialdried over Na2SO4
- customAfter removing the solvent
- customchromatographed
- washeluting with ethyl acetate/methanol/triethylamine 87/10/3
Sources & evidence
- ORD record
- ord-4ee1e6cc4d484a91bb20fa0357b638cb
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06951848B2
Reaction notes
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