Ethylenediamine → 4-[(Triethoxysilyl)methyl]morpholine

HRID 1879426Notes

Reaction equation

HRID 1879426 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[CH2:8][Si:9]([O:16][CH2:17][CH3:18])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12].C(N)CN>>[CH2:14]([O:13][Si:9]([CH2:8][N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)([O:16][CH2:17][CH3:18])[O:10][CH2:11][CH3:12])[CH3:15]

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 8083MorpholineHCID 84858Silane, (chloromethyl)triethoxy-

Product 1

HCID 124198814-[(Triethoxysilyl)methyl]morpholineYield 68.7%

Procedure

82 g of dry morpholine (pKb 5.67) were heated to 120° C. in a 500 ml four-necked flask having a reflux condenser, KPG stirrer and thermometer and 80 g of chloromethyltriethoxysilane were added in the course of 180 min with stirring. After the end of the addition, the temperature was reduced to 105° C. and 56.6 g of ethylenediamine (pKb 4.07) were added to the mixture in the course of 10 min with stirring, phase separation occurring. At constant temperature, stirring was effected for a further 30 min and the heavier ethylenediamine hydrochloride phase was then separated off. The upper phase was subjected to fractional distillation. 68 g (yield 68%) of 4-(triethoxysilylmethyl)tetrahydro-1,4-oxazine were obtained, the purity of which was determined as 98.4% by gas chromatography.

Workup

  1. additionAfter the end of the addition
  2. customwas reduced to 105° C.
  3. stirringwith stirring
  4. customphase separation
  5. stirringAt constant temperature, stirring
  6. customthe heavier ethylenediamine hydrochloride phase was then separated off
  7. distillationThe upper phase was subjected to fractional distillation

Sources & evidence

ORD record
ord-e508e05ee85d4bfab6f09f546aabba55
Source dataset
uspto-grants-2012_11
Patent number
US08314263B2

Reaction notes

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