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

HRID 1592370Notes

Reaction equation

HRID 1592370 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.C(N(C(C)C)CC)(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 diisopropylethylamine (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-7a91e609f6274606a71c948f570c6228
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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