N-Methylbutylamine → HCID 86684956, compound

HRID 2273170Notes

Reaction equation

HRID 2273170 reaction equation
Cl[SiH:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[CH:5]=[CH:4][N:3]1[C:11]([CH3:14])([CH3:13])[CH3:12].[CH2:15]([N-]C)[CH2:16][CH2:17][CH3:18].[Li+].CCCCCC.C([Li])CCC.[CH2:33]([NH:37]C)CCC>CCCCCC.O1CCCC1>[C:11]([N:3]1[CH:4]=[CH:5][N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[Si:2]1([NH:37][CH3:33])[CH2:15][CH2:16][CH2:17][CH3:18])([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 8068N-MethylbutylamineHCID 23670121HCID 23670121, compoundHCID 713346111,3-Di-tert-butyl-2-chloro-2,3-dihydro-1H-1,3,2-diazasiloleHCID 178418244HCID 178418244, compound

Product 1

HCID 86684956HCID 86684956, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

In an argon atmosphere, 5.50 g (23.6 mmol) of Si(tBuNCHCHNtBu)(H)Cl was dissolved in 10 mL of hexane and after adding a lithium butyl(methyl)amide solution (prepared by mixing 14.2 mL of 1.67 mol/L butyllithium hexane solution, 15 mL of tetrahydrofuran and 2.07 g of N-butyl-N-methylamine and stirring the mixture at room temperature for 1 hour), the mixture was stirred at room temperature for 20 hours. Insoluble matters produced were separated by filtration, and the solvent was removed by distillation from the filtrate under atmospheric pressure. The obtained residue was distilled under reduced pressure (distillation temperature: 109° C./3.3×102 Pa) to obtain 1,3-di-tert-butyl-2-butylmethylamino-1,3-diaza-2-silacyclopent-4-ene (Si(tBuNCHCHNtBu)(H)NBuMe) as a colorless liquid (yielded amount: 5.67 g, yield: 85%).

Workup

  1. customprepared
  2. stirringwas stirred at room temperature for 20 hours
  3. customInsoluble matters produced
  4. customwere separated by filtration
  5. customthe solvent was removed by distillation from the filtrate under atmospheric pressure
  6. distillationThe obtained residue was distilled under reduced pressure (distillation temperature: 109° C./3.3×102 Pa)
  7. customto obtain

Sources & evidence

ORD record
ord-15f77a5a7cde4de897056e65e4c36539
Source dataset
uspto-grants-2015_09
Patent number
US09120825B2

Reaction notes

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