Water → HCID 69344008, compound

HRID 590538Notes

Reaction equation

HRID 590538 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:16][CH2:17][Si:18]([CH2:21][CH2:22]Br)([CH3:20])[CH3:19].O>ClCCl>[CH2:1]([N:8]1[CH2:22][CH2:21][Si:18]([CH3:20])([CH3:19])[CH2:17][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 12169348Bis(2-bromoethyl)(dimethyl)silane

Product 1

HCID 69344008HCID 69344008, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzylamine (17.56 g, 0.16 mol) and K2CO3 (3.4 g, 24.6 mmol) are added to a solution of bis(2-bromoethyl)dimethylsilane 2(4.0 g, 16.4 mmol) in Dichloromethane (DCM). The mixture is then refluxed for 16 h. Water is added and the aqueous layer is extracted with DCM. It is then washed with 5% sodiumhydroxide (NaOH) solution, dried and concentrated. The product is purified by column chromatography on silica using hexane-ethylacetate mixtures to obtain the product as a colorless liquid 3 (2.1 g) in 59% yield.

Workup

  1. temperatureThe mixture is then refluxed for 16 h
  2. extractionthe aqueous layer is extracted with DCM
  3. washIt is then washed with 5% sodiumhydroxide (NaOH) solution
  4. customdried
  5. concentrationconcentrated
  6. customThe product is purified by column chromatography on silica

Sources & evidence

ORD record
ord-0062cea83da548a190c00b6c7564fcb6
Source dataset
uspto-grants-2016_01
Patent number
US09233989B2

Reaction notes

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