CS252619B1 - N- (alkoxysilylpropyl) (1-phenylethyl) amines - Google Patents

Abstract

N-(Alkoxysilylpropyl)(1-phenylethyl)- amines of the general formula (R4)2R^si(CH2)3NHCH- -(CH3)C6H5, where R1 represents an alkoxy group of one to four carbon atoms and R2 has the same meaning as R4 or denotes methyl. These new substances are suitable reagents for introducing a sec.amine group onto the surface of inorganic supports.

Description

The invention relates to novel N- (alkoxysilylpropyl) (1-phenylethyl) amines.

It is known that in many fields of applied chemistry, such as heterogeneization of homogeneous catalysts, enzyme binding, in filled polymer composites or chromatography, surface functionalized materials by suitable groups are used. One such group is the secamino group. The compounds of the invention are agents which make it possible to introduce sec-amine groups very readily on the surface of the carrier.

The present invention provides N- (alkoxysilylpropyl) (1-phenylethyl) -amines of the general formula (R ¹ ) 2 R ² Si (CH 2) ₃ NH-CH (CH ₃ ) C ₆ H ₅ wherein R 2 represents a C 1 -C 4 alkoxy group and R ² has the same meaning as R ⁴ or represents methyl.

These novel compounds can be prepared, for example, by reacting 1-phenylethylamine with (3-chloropropyl) alkoxysilane or (3-bromopropyl) alkoxysilane of the formula (ft ¹ , 2R ² Si (CH 2) ₃ x where X is chlorine or bromine and the other symbols have the above importance.

Reaction according to equation (r ¹ ) 2r ^{2 s} (ch2) ₃ x + h ₂ nch (ch ₃ ) c ₆ h ₅ -> (r ¹ ) 2r ^{2 s} (ch2) ₃ nhch <ch ₃ ) c ₆ h ₅ + HX can be carried out in aprotic solvents such as dioxane, dibutyl ether, toluene, nitromethane, optionally without solvent, and is accelerated by elevated temperature. The ratio of the reactants is governed by the stoichiometry of the reaction. However, it is possible to work with an excess of one of the reactants, preferably with an excess of amine, since not only the hydrogen halide formed is bound, but the formation of the tertiary amine formed in the next stage of the reaction is also suppressed.

An advantage of the properties of the compounds described in the invention is that optically active 1-phenyl-ethylamine can be used as the starting amine, and optically active N- (alkoxylylpropyl) (1-phenylethyl) amines are also the product of the reaction.

The following examples characterize the compounds of the invention without limiting or restricting it.

Example 1

To 0.3 mol of D-1- (phenyl) ethylamine was added 0.1 mol of (3-chloropropyl) triethoxysilane and the mixture was heated to 130 ° C for 10 h. Then it was diluted with toluene, the precipitate filtered off and the filtrate distilled. After distilling off the low-boiling components, N- [3- (triethoxysilyl) propyl] (1-phenylethyl) -amine was obtained by distillation under vacuum, b.p. 100 to 120 ° C / 1 to 15 Pa in 30% yield.

In its infrared spectrum, a small band was found at 3,310 cm ^-1 corresponding to) (NH), a multiplet centered at 1,100 corresponding to 1> as (Si-OC), vibrations corresponding to aliphatic CH2 and CH3 groups at 2,920, 2970 and 2,870 cm ^-1 . ^{The 13} C NMR spectrum shows a signal corresponding to the Gi-CH 2 group (d = 7.9), the CH ₂ -NH group (f f = 50.5) and the phenyl group (~ 145.8; 128.2; 126.6 and 126, 4). The product solution in benzene rotated the plane of polarized light (// ²² $ 4 $ = 16.5 ± 1 °, c = 4.8 (benzene)).

Example 2

Example 1 was repeated except that (3-chloropropyl) triethoxysilane was used (3-bromopropyl) trimethoxysilane and the starting amine was racemic. N- (3- (Trimethoxysilyl) propyl) (1-phenylethyl) amine was obtained in a yield of 28%. in its infrared and? c nmr spectrum, the bands and signals shown in Example 1 were found.

Example 3

Example 2 was repeated except that (3-chloropropyl) (methyl) diethoxysilane was used instead of (3-bromopropyl) trimethoxysilane. N- (3- (diethoxymethylsilyl) propyl) (1-phenylethyl) amine was obtained in a yield of 31%. The bands and signals shown in Example 1 were found in its IR and ¹³ C NMR spectra.

Example 4

Example 2 was repeated except that (3-chloropropyl) (methyl) dimethoxysilane was used instead of (3-bromopropyl) trimethoxysilane. N- (3- (dimethoxymethylsilyl) propyl) (1-phenylethyl) amine was obtained in a yield of 29%. The bands and signals shown in Example 1 were found in its infrared and @ ²⁰ NMR spectra.

Claims (1)

SUBJECT OF THE INVENTION N- (Alkoxysilylpropyl) (1-phenylethyl) amines of formula (R · '·) ₂ ^{R 2} Si _(CH) 3 NHCH2 (CH-j) CGH: wherein ^R1 is alkoxy of one to four carbon atoms, R ² is defined as R ¹ or denotes methyl.