Tert-Butylamine → N-tert-Butyl-N-(trimethylsilylmethyl)amine

HRID 29721Notes

Reaction equation

HRID 29721 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:7][Si:8]([CH3:11])([CH3:10])[CH3:9].[OH-].[Na+]>>[C:1]([NH:5][CH2:7][Si:8]([CH3:11])([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 6385Tert-ButylamineHCID 14798Sodium HydroxideHCID 75361Silane, (chloromethyl)trimethyl-

Product 1

HCID 425246N-tert-Butyl-N-(trimethylsilylmethyl)amine

Conditions

Temperature
200 °C

Procedure

A mixture of tert-butylamine (18.0 mL, 171 mmol) and (chloromethyl)trimethylsilane (7.00 g, 57.1 mmol) was heated in a thick-walled glass tube at 200° C. overnight. After cooling to ambient temperature, the reaction mixture was poured into 1 N NaOH and extracted three times with diethyl ether. The combined organic extracts were washed with brine, dried (MgSO4), and the volatiles evaporated in vacuo. Distillation (atmospheric pressure; ˜135° C.) of the residual liquid gave the title compound 77 as a colorless liquid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionextracted three times with diethyl ether
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe volatiles evaporated in vacuo
  6. distillationDistillation (atmospheric pressure; ˜135° C.) of the residual liquid

Sources & evidence

ORD record
ord-043b0c3cc51046faa4d80dcc8ff53bfc
Source dataset
uspto-grants-2008_09
Patent number
US07419990B2

Reaction notes

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