4-Methylmorpholine → 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

HRID 1782555Notes

Reaction equation

HRID 1782555 reaction equation
O.ON1C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.CN1CCOCC1.Cl.[CH3:29][N:30]([CH3:39])[CH2:31][CH2:32][CH2:33][N:34]=[C:35]=[N:36][CH2:37][CH3:38]>C(Cl)Cl.CN(C=O)C>[CH3:38][CH2:37][N:36]=[C:35]=[N:34][CH2:33][CH2:32][CH2:31][N:30]([CH3:39])[CH3:29]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 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 primary or secondary amine (1 equivalent), a carboxylic acid (1.1-2.0 equivalents), 1-hydroxy-benzotriazole hydrate (HOBT) (1.1-2.0 equivalents) and DIPEA (DIPEA) or N-methylmorpholine (NMM) (1.5-3 equivalents) in CH2Cl2 or DMF (concentration ˜0.05-1.5M) was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDCI) (1.1-2.0 equivalents). The solution was stirred at room temperature for 1-3 days and concentrated in vacuo. In a standard work-up, the mixture was diluted with CH2Cl2 or EtOAc and washed consecutively with saturated aqueous NaHCO3 and brine. The organic layer was dried (Na2SO4 or MgSO4), filtered and concentrated under reduced pressure. The crude material was purified by flash column chromatography or by radial chromatography on silica gel.

Workup

  1. concentrationconcentrated in vacuo
  2. additionIn a standard work-up, the mixture was diluted with CH2Cl2 or EtOAc
  3. washwashed consecutively with saturated aqueous NaHCO3 and brine
  4. dry with materialThe organic layer was dried (Na2SO4 or MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by flash column chromatography or by radial chromatography on silica gel

Sources & evidence

ORD record
ord-94f397f67f214014938c0a85f19d4fca
Source dataset
uspto-grants-2009_03
Patent number
US07498346B2

Reaction notes

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