Ethylenediamine → 4-[(Triethoxysilyl)methyl]morpholine
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>>[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[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
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 226.6 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 without a distillation column. 37 g (45% recovery) of morpholine having a purity of 89.7% and 73.5 g (yield 74.2%) of 4-(triethoxysilylmethyl)-tetrahydro-1,4-oxazine were obtained, the purity of which was determined as 97.3%.
Workup
- additionAfter the end of the addition
- customwas reduced to 105° C.
- stirringwith stirring
- customphase separation
- stirringAt constant temperature, stirring
- customthe heavier ethylenediamine hydrochloride phase was then separated off
- distillationThe upper phase was subjected to fractional distillation without a distillation column
Sources & evidence
- ORD record
- ord-2112643ff15446519237a9eeddb63b23
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08314263B2
Reaction notes
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