Iodoethane → 6-hydroxy-3-(ethyl)amino-1,2,3,4-tetrahydro-9H-carbazole 6-benzyloxy-3-(ethyl)amino-1,2,3,4-tetrahydro-9H-carbazole

HRID 726385Notes

Reaction equation

HRID 726385 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][CH3:31]>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][CH3:31])[CH2:13][C:12]2=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[OH: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][CH3:31])[CH2:13][C:12]2=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 226113086-benzyloxy-3-amino-1,2,3,4-tetrahydro-9H-carbazole

Product 1

HCID 197107266-hydroxy-3-(ethyl)amino-1,2,3,4-tetrahydro-9H-carbazole 6-benzyloxy-3-(ethyl)amino-1,2,3,4-tetrahydro-9H-carbazoleYield 21.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.225 gm (0.77 mMol) 6-benzyloxy-3-amino-1,2,3,4-tetrahydro-9H-carbazole in 20 mL acetonitrile were added 0.223 gm (1.617 mMol) potassium carbonate followed by 130 μL (1.617 mMol) iodoethane and the reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was then heated at 60° C. for 4 hours and then at 50°-45° C. for 3 hours. The reaction mixture was then concentrated under reduced pressure and the residue partitioned between dichloromethane and water. The organic phase was then dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to radial chromatography (silica gel, 2 mm), eluting with 97:3:1 dichloromethane:methanol:ammonium hydroxide. Fractions shown to contain the desired compound were concentrated under reduced pressure to give 0.045 gm (6%) of the desired compound.

Workup

  1. temperatureThe reaction mixture was then heated at 60° C. for 4 hours
  2. waitat 50°-45° C. for 3 hours
  3. concentrationThe reaction mixture was then concentrated under reduced pressure
  4. customthe residue partitioned between dichloromethane and water
  5. dry with materialThe organic phase was then dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluting with 97:3:1 dichloromethane
  8. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-e54905de49ae434b9c091c0c02635cbd
Source dataset
uspto-grants-1998_01
Patent number
US05708187

Reaction notes

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