Chloride → N-[(Ethoxydimethylsilyl)methyl]cyclohexanamine

HRID 2220554Notes

Reaction equation

HRID 2220554 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:9][Si:10]([O:13][CH2:14][CH3:15])([CH3:12])[CH3:11].[Cl-]>>[CH:1]1([NH:7][CH2:9][Si:10]([O:13][CH2:14][CH3:15])([CH3:12])[CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 312ChlorideHCID 7965CyclohexylamineHCID 26073Silane, (chloromethyl)ethoxydimethyl-

Product 1

HCID 15965763N-[(Ethoxydimethylsilyl)methyl]cyclohexanamineYield 61%

Conditions

Temperature
30 °C

Procedure

In a 500 ml three-necked flask having a reflux condenser, KPG stirrer and thermometer, 176 g of commercial cyclohexylamine (water content ≦2%) were heated to 100° C., and 122 g of (chloromethyl)ethoxydimethylsilane were added over the course of 30 min with stirring. After the end of the addition, the mixture was stirred for two hours under reflux and cooled to 30° C., and the white precipitate formed was filtered using a pressure filter, and rinsed with cyclohexylamine. Filtrate and wash solutions were combined and were freed from excess cyclohexylamine under reduced pressure. The subsequent fractional distillation gave 105 g (yield 61%) of (N-cyclohexylaminomethyl)ethoxydimethylsilane having a chloride content of 600 ppm.

Workup

  1. customIn a 500 ml three-necked flask having
  2. additionAfter the end of the addition
  3. stirringthe mixture was stirred for two hours
  4. temperatureunder reflux
  5. customthe white precipitate formed
  6. filtrationwas filtered
  7. filtrationfilter
  8. washrinsed with cyclohexylamine
  9. washFiltrate and wash solutions
  10. distillationThe subsequent fractional distillation

Sources & evidence

ORD record
ord-ea0d39c98e564b0795e6f12dbc434a17
Source dataset
uspto-grants-2008_08
Patent number
US07417160B2

Reaction notes

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