1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86649436, compound

HRID 383883Notes

Reaction equation

HRID 383883 reaction equation
[CH:1]([O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].Cl.C(N=C=NCCCN(C)C)C.CCN=C=NCCCN(C)C.[C:35]([O:39][C:40]([N:42]1[CH2:47][C@H:46]2[CH2:48][CH2:49][C@@H:43]1[C@H:44]([C:50](O)=[O:51])[CH2:45]2)=[O:41])([CH3:38])([CH3:37])[CH3:36]>N1C=CC=CC=1>[CH:1]([O:4][C:5]1[CH:11]=[CH:10][C:8]([NH:9][C:50]([C@H:44]2[C@H:43]3[CH2:49][CH2:48][C@H:46]([CH2:47][N:42]3[C:40]([O:39][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:41])[CH2:45]2)=[O:51])=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 821124-IsopropoxyanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68427145HCID 68427145, compound

Product 1

HCID 86649436HCID 86649436, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Isopropoxyaniline (1.49 g, 9.87 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (hereinafter, “WSC”; 1.89 g, 9.87 mmol) were added to a pyridine (20 mL) solution of the compound (1.68 g, 6.58 mmol) synthesized in (2), and the mixture was stirred at room temperature for 14 hours. The reaction mixture was concentrated under reduced pressure, and, after addition of ethyl acetate, washed once with distilled water, once with 1 N-hydrochloric acid aqueous solution, and once with 1N-sodium hydroxide aqueous solution. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was then purified using silica gel column chromatography to obtain the target (1.26 g, 49%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionafter addition of ethyl acetate
  3. washwashed once with distilled water, once with 1 N-hydrochloric acid aqueous solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was then purified
  7. customto obtain the target (1.26 g, 49%)

Sources & evidence

ORD record
ord-1fe0d58309b6448482cee54c291ddf6b
Source dataset
uspto-grants-2013_02
Patent number
US08367698B2

Reaction notes

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