1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 33086887, compound

HRID 1668524Notes

Reaction equation

HRID 1668524 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.[N:11]1([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[CH3:1][C:2]1[N:7]=[C:6]([C:8]([N:14]2[CH2:13][CH2:12][N:11]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15]2)=[O:10])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 702826-Methylpyridine-2-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 33086887HCID 33086887, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Methylpicolinic acid (2.15 g) and t-butyl piperazine-1-carboxylate (3.21 g) was dissolved in 45 mL of DMF, and 4.24 g of HOBt was added to the solution at ice temperature. After stirring for 15 minutes, additionally 3.0 g of WSC was added thereto and the mixture was stirred at room temperature overnight. After the solvent was removed under reduced pressure from the reaction mixture, then water was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, then the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel (methylene chloride-ethanol=30:1) to give 4.57 g of t-butyl 4-(6-methylpyridine-2-carbonyl)piperazine-1-carboxylate as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customAfter the solvent was removed under reduced pressure from the reaction mixture
  3. additionwater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by chromatography on silica gel (methylene chloride-ethanol=30:1)

Sources & evidence

ORD record
ord-4e55d3e9d6ce40f5b66f2e8c10fa27b0
Source dataset
uspto-grants-2011_08
Patent number
US07989446B2

Reaction notes

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