2,6-Lutidine → N-{[1-(3-methoxypropyl)-4-methyl-1H-indol-3-yl]methyl}cyclopropanamine

HRID 872031Notes

Reaction equation

HRID 872031 reaction equation
FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[CH:13]1([N:16]([CH2:24][C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][C:32]=3[CH3:34])[N:27]([CH2:35][CH2:36][CH2:37][O:38][CH3:39])[CH:26]=2)C(=O)OC(C)(C)C)[CH2:15][CH2:14]1.N1C(C)=CC=CC=1C.C(=O)(O)[O-].[Na+]>ClCCl.CO>[CH3:39][O:38][CH2:37][CH2:36][CH2:35][N:27]1[C:28]2[C:33](=[C:32]([CH3:34])[CH:31]=[CH:30][CH:29]=2)[C:25]([CH2:24][NH:16][CH:13]2[CH2:14][CH2:15]2)=[CH:26]1

Participants

7

Reactant 4

HCID 79372,6-LutidineHCID 65367Trimethylsilyl triflateHCID 516892Sodium BicarbonateHCID 59494370tert-butyl cyclopropyl{[1-(3-methoxypropyl)-4-methyl-1H-indol-3-yl]methyl}carbamate

Product 1

HCID 59494170N-{[1-(3-methoxypropyl)-4-methyl-1H-indol-3-yl]methyl}cyclopropanamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Trimethylsilyl trifluoromethanesulfonate (213 μL) was added to a solution of tert-butyl cyclopropyl{[1-(3-methoxypropyl)-4-methyl-1H-indol-3-yl]methyl}carbamate (175 mg and 2,6-lutidine (192 μL) in dichloromethane (7 ml) under ice-cooling and the mixture was stirred at room temperature for 15 minutes. A saturated aqueous solution of sodium bicarbonate and methanol were added successively to the reaction mixture and the mixture was further stirred at the same temperature for 30 minutes. The reaction mixture was extracted with chloroform and the organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated in vacuo. The resulted residue was purified with a silica gel column chromatography (eluting solvent: ethyl acetate/methanol=95/5 to 70/30) to give N-{[1-(3-methoxypropyl)-4-methyl-1H-indol-3-yl]methyl}cyclopropanamine (106 mg) as a colorless oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred at the same temperature for 30 minutes
  3. extractionThe reaction mixture was extracted with chloroform
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulted residue was purified with a silica gel column chromatography (eluting solvent: ethyl acetate/methanol=95/5 to 70/30)

Sources & evidence

ORD record
ord-636f8f88832f4dfa8e4f04df3e8783b5
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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