Diisopropylethylamine → 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

HRID 1784170Notes

Reaction equation

HRID 1784170 reaction equation
Cl.[CH3:2][N:3]([CH3:12])[CH2:4][CH2:5][CH2:6][N:7]=[C:8]=[N:9][CH2:10][CH3:11].O.ON1C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[CH3:11][CH2:10][N:9]=[C:8]=[N:7][CH2:6][CH2:5][CH2:4][N:3]([CH3:12])[CH3:2]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of a 1° or 2° amine (0.1-0.3 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDCI) (1.5 equiv.), 1-hydroxy-benzotriazole hydrate (HOBT) (1.5 equiv.), and DIPEA (2.0 equiv.) in CH2Cl2 or DMF (0.05 M), was added a carboxylic acid (1.0-2.0 equiv). The solution was stirred for 16 h at ambient temperature. The reaction was quenched with saturated NaHCO3 solution and extracted three times with CH2Cl2. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The resultant crude material was purified on a silica gel column (5% MeOH/CH2Cl2).

Workup

  1. customThe reaction was quenched with saturated NaHCO3 solution
  2. extractionextracted three times with CH2Cl2
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resultant crude material was purified on a silica gel column (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-a9702d90bae74da6bc9d268af5983ca1
Source dataset
uspto-grants-2009_03
Patent number
US07501518B2

Reaction notes

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