1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-[1-(Tert-butoxycarbonyl)piperidine-4-carbonylamino]indole

HRID 20981

Reaction equation

HRID 20981 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.[C:33]([O:37][C:38]([N:40]1[CH2:45][CH2:44][CH:43]([C:46](O)=[O:47])[CH2:42][CH2:41]1)=[O:39])([CH3:36])([CH3:35])[CH3:34]>CN(C=O)C.O>[C:33]([O:37][C:38]([N:40]1[CH2:45][CH2:44][CH:43]([C:46]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)=[O:47])[CH2:42][CH2:41]1)=[O:39])([CH3:36])([CH3:35])[CH3:34]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 788675-AminoindoleHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 684936015-[1-(Tert-butoxycarbonyl)piperidine-4-carbonylamino]indoleYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5-Aminoindole (100 mg, 0.757 mmol) was dissolved in DMF (2 mL), and the solution was added with EDCI (290 mg, 1.51 mmol), HOBT monohydrate (102 mg, 0.755 mmol) and 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (208 mg, 0.907 mmol), followed by stirring at room temperature for 2 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with 1 mol/L hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by slurry using acetonitrile to obtain 5-[1-(tert-butoxycarbonyl)piperidine-4-carbonylamino]indole (142 mg, yield 55%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 1 mol/L hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by slurry

Sources & evidence

ORD record
ord-b381727ee5a445ea96e3daa9d28cbe44
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

Loading…