1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57385047, compound

HRID 83597Notes

Reaction equation

HRID 83597 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([OH:18])=O)=[CH:4][CH:3]=1.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[NH:52]1[CH2:57][CH2:56][CH:55]([C:58]([O:60][CH2:61][CH3:62])=[O:59])[CH2:54][CH2:53]1>C(Cl)Cl.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:52]2[CH2:57][CH2:56][CH:55]([C:58]([O:60][CH2:61][CH3:62])=[O:59])[CH2:54][CH2:53]2)=[O:18])=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70770Ethyl 4-piperidinecarboxylateHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 223108991-(4-Chlorobenzyl)-1H-indole-2-carboxylic acid

Product 1

HCID 57385047HCID 57385047, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(4-chlorobenzyl)-1H-indole-2-carboxylic acid (2.4 g, 8.40 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (2.4 g, 12.60 mmol), and 1-Hydroxybenzotriazole hydrate (1.9 g, 12.60 mmol) were dissolved in 20.0 mL of DCM. The resulting suspension was stirred for twenty minutes where it turned into a clear, yellow solution. N,N-Diisopropylethylamine (2.2 mL, 12.60 mmol) and ethyl piperidine-4-carboxylate (1.94 mL, 12.60 mmol) were added to the reaction. The reaction was stirred overnight. Water was added to the reaction followed by ethyl acetate. The layers were separated and the organic layer was washed sequentially with 1N HCl, saturated sodium bicarbonate, and saturated sodium chloride. The organic layer was dried over magnesium sulfate, filtered and concentrated. The resulting crude mixture was triturated with diethyl ether to obtain pure product as a white solid. Yield: 2.79 g, (White solid)

Workup

  1. stirringThe reaction was stirred overnight
  2. customThe layers were separated
  3. washthe organic layer was washed sequentially with 1N HCl, saturated sodium bicarbonate, and saturated sodium chloride
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting crude mixture was triturated with diethyl ether
  8. customto obtain pure product as a white solid

Sources & evidence

ORD record
ord-35b54fda9c3a4b158ffd6c2bbb3d8f0d
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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