Diisopropylethylamine → HCID 23043521, compound

HRID 2165043Notes

Reaction equation

HRID 2165043 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:13])[CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][C:8]1=[O:12].Br[CH2:15][CH2:16][Si:17]([CH2:20][CH2:21]Br)([CH3:19])[CH3:18].CCN(C(C)C)C(C)C>C(Cl)(Cl)Cl>[CH3:18][Si:17]1([CH3:19])[CH2:20][CH2:21][N:1]([CH2:2][CH2:3][NH:4][C:5](=[O:13])[CH2:6][N:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[O:12])[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12169348Bis(2-bromoethyl)(dimethyl)silaneHCID 19908624HCID 19908624, compound

Product 1

HCID 23043521HCID 23043521, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1.90 g (10.3 mmol) of N-(2-aminoethyl)-2-oxo-1-pyrrolidineacetamide, 2.76 g (10.1 mmol) of bis(2-bromoethyl)dimethylsilane, 5.20 g of Huenig base, and 20 ml of chloroform was stirred and then the solvent was removed in vacuo. The resulting mixture was heated at 100°-105° C. for 8 hours. Aqueous NaHCO3 was added to the cooled reaction mixture, and the aqueous solution was extracted with chloroform. The dried chloroform solution was concentrated in vacuo and chromatographed on silica gel column to afford 450 mg (Yield: 15.0%) of the desired compound.

Workup

  1. customthe solvent was removed in vacuo
  2. temperatureThe resulting mixture was heated at 100°-105° C. for 8 hours
  3. additionAqueous NaHCO3 was added to the cooled reaction mixture
  4. extractionthe aqueous solution was extracted with chloroform
  5. concentrationThe dried chloroform solution was concentrated in vacuo
  6. customchromatographed on silica gel column

Sources & evidence

ORD record
ord-2e8b07e7f01d404396ceb0de31adc2bc
Source dataset
uspto-grants-1990_07
Patent number
US04939126

Reaction notes

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