Benzylamine → HCID 69344008, compound

HRID 590542Notes

Reaction equation

HRID 590542 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.Br[CH2:17][CH2:18][Si:19]([CH2:22][CH2:23]Br)([CH3:21])[CH3:20].[OH-].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:23][CH2:22][Si:19]([CH3:21])([CH3:20])[CH2:18][CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 12169348Bis(2-bromoethyl)(dimethyl)silane

Product 1

HCID 69344008HCID 69344008, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Benzylamine (20 mL, 182 mmol) and Et3N (15.2 mL, 109 mmol) are added to a solution of bis-(bromomethyl) dimethylsilane 2 (10 g, 36.5 mmol) in chloroform (100 mL). The mixture is then refluxed for 16 h. 5% sodiumhydroxide solution (150 mL) is then added and the aqueous layer is extracted with dichloromethane (DCM, 2×100 mL). It is then washed with brine (200 mL), dried and concentrated. The product is purified by column chromatography on silica gel using hexane-EtOAc mixtures to obtain the product 3 as a light yellow liquid (4.3 g) in 54% yield.

Workup

  1. temperatureThe mixture is then refluxed for 16 h
  2. extractionthe aqueous layer is extracted with dichloromethane (DCM, 2×100 mL)
  3. washIt is then washed with brine (200 mL)
  4. customdried
  5. concentrationconcentrated
  6. customThe product is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-84d65ef269c14cfba2c10ca33cdf2e85
Source dataset
uspto-grants-2016_01
Patent number
US09233989B2

Reaction notes

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