Potassium Carbonate → 6-benzyloxy-3-(propyl)amino-1,2,3,4-tetrahydro-9H-carbazole

HRID 726386Notes

Reaction equation

HRID 726386 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]1[CH2:16][CH2:15][CH:14]([NH2:22])[CH2:13][C:12]2=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:30][CH2:31][CH3:32]>C(#N)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]1[CH2:16][CH2:15][CH:14]([NH:22][CH2:30][CH2:31][CH3:32])[CH2:13][C:12]2=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-Iodopropane2×HCID 226113086-benzyloxy-3-amino-1,2,3,4-tetrahydro-9H-carbazole

Product 1

HCID 226113906-benzyloxy-3-(propyl)amino-1,2,3,4-tetrahydro-9H-carbazoleYield 39.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.600 gm (2.05 mMol) 6-benzyloxy-3-amino-1,2,3,4-tetrahydro-9H-carbazole in 35 mL acetonitrile were added 0.283 gm (2.05 mMol) potassium carbonate followed by 240 μL (2.46 mMol) iodopropane and the reaction mixture was stirred at room temperature for 2.5 days. Additional iodopropane was added and the reaction stirred at room temperature until all of the starting material had been consumed. The reaction mixture was then partitioned between dichloromethane and water. The aqueous phase was extracted with dichloromethane and the combined organic phases were then dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 96.5:3:0.5 dichloromethane:isopropanol:ammonium hydroxide. Fractions shown to contain the desired compound were concentrated under reduced pressure to give 0.270 gm (39%) of the desired compound.

Workup

  1. stirringthe reaction stirred at room temperature until all of the starting material
  2. customhad been consumed
  3. customThe reaction mixture was then partitioned between dichloromethane and water
  4. extractionThe aqueous phase was extracted with dichloromethane
  5. dry with materialthe combined organic phases were then dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluting with 96.5:3:0.5 dichloromethane
  8. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-7e1dd54b97814590bbad6cbcc43dadc3
Source dataset
uspto-grants-1998_01
Patent number
US05708187

Reaction notes

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