CS275660B6 - 1-alkylamino-3-decyloxy-2-propanol - Google Patents

Abstract

The solution relates to new alkanolamines of the general formula I, where R represents methyl, ethyl, propyl, isopropyl, butyl and isobutyl. 1-Alkylamino-3-decyloxy-2-propanols have industrial use as intermediates for the production of heterocyclic antimicrobial surfactants.

Description

The invention relates to 1-alkylamino-3-decyloxy-2-propanols. ·

Substituted alkanolamines are a suitable intermediate in the production of heterocyclic antimicrobial surfactants [N. S. Bodor, 3. 3. Kaminski: Chem. Abstr. 85, 46640s (1976); N. S. Bodor, 3. J. Kaminski: Chem. Abstr. 84. 44083t / 1976 /]. Most often, 1-alkylamino-3-chloro-2-propanols from alkylamines and chloromethyloxirane, or 1-alkylamino-2-propanols from alkylamines and methyloxirane príprav are prepared. B. Kelvey, B. G. Webre, R. R. Benerito: 3. Org. Chem. 25, 1424 (1960); 3. B. Kelvey, B. G. Webre, E. Klein: 3. Org. Chem. 24, 614/1959]. Ethanol or water is most often used as the solvent [N. H. Cromwell, N. G. Barker: 3. Am. Chem. Soc. 72, 4110 (1950); A. F. McKay, Η. H. Brownell: 3. Org. Chem. 15, 648 (1950); T. Colclough, 3. I. Cuneen, C. G. Moore: Tetrahedron 15, 187 (1961)]. The reaction is catalyzed by compounds with a hydroxyl group [I. T. Smith: Polymer 2, 95 (1961 /], the reaction product - alkanolamine [L. Shechter, 3. Wynstra, R.P. Kurjy: Ind. Eng. Chem. 48, 94 (1956)].

The 1-alkylamino-3-decyloxy-2-propanols prepared by us have not been known or described so far.

The invention relates to 1-alkylamino-3-decyloxy-2-propanols of the general formula I r-nh-ch ₂ -ch-ch ₂ -o- (ch ₂ ) ₉ -ch ₃

OH (1) wherein R represents methyl, ethyl, propyl, isopropyl, butyl and isobutyl.

The advantage of these substances is that they contain a secondary amino group and a hydroxy group on adjacent carbons, so they can be used for cyclization reactions with carbonyl compounds.

Example 1

^{A solution of 21.7 g (0.1 mol) of decyloxymethyloxirane in 50 cm 3 of} ethanol is added to 50 cm ^{3 of a} saturated solution of methylamine in ethanol with stirring at 25 DEG C. over a period of 1 hour, and the mixture is stirred for a further 10 hours. The ethanol and unreacted methylamine are then distilled off to dryness at a pressure of 3 kPa and a temperature of 40 ° C. 200 cm ^{3 of} distilled water with 10 cm ^{3 of} 30 wt. % aqueous hydrochloric acid solution. The resulting aqueous solution of 1-methylamino-3-decyloxy-2-propanol hydrochloride is purified by extraction with ether (twice 100 cm ³ ). The free alkanolamine is obtained by adding a solution of 10 g of sodium bicarbonate in 50 cm ^{3 of} water and extracting with 3 ethers (twice per 100 cm 3). After drying the ether extract over anhydrous sodium sulfate, the ether was distilled off. The 1-methylamino-3-decyloxy-2-propanol thus prepared does not require further purification. Yield 87%, i.e. 21.3 g of 1-methylamino-3-decyloxy-2-propanol. The IR spectrum, said determining bands: 3620, 3320, 2953, 2918, 2850, 2805, 1465, 1383, 1226, 1170, 1125, 1108, 1079, 1041 and 724 cm ^- '''. In the mass spectrum, the following determining peaks are: 246, 245, 118, 104 and 88.

Elemental analysis for ^ - ^ Η ^ Ο ^, molecular weight ’245 calculated: 68.57 wt. % carbon, 12.65 wt. % hydrogen, 5.71 wt. % nitrogen found: 68.48 wt. % carbon, 12.77 wt. % hydrogen, 6.65 wt. % nitrogen.

Example 2

The procedure is as in Example 1, except that 50 cm ^{3 of a} saturated solution of ethylamine in ethanol are used. The yield is 90%, i.e. 23.3 g of 1-ethylamino-3-decyloxy-2-propanol. In the infrared spectrum, the determining absorption bands are identical to the spectrum in Example 1. In the mass spectrum, the following determining peaks are: 260, 259, 132, 118 and 102.

Elemental analysis for C % carbon, 12.74 wt. % hydrogen, 5.41 wt. % nitrogen found: 69.34 wt. % carbon, 12.83 wt. % hydrogen, 5.38 wt. % nitrogen.

CS 275 660 B6

Example 3

The procedure is as in Example 1, except that 8.9 g (0.15 mol) of propylamine in 20 cm ^{3 of} ethanol are used. The yield is 85%, i.e. 23.2 g of 1-propylamino-3-decyloxy-2-propanol. The infrared spectrum is the same as in Example 1. In the mass spectrum, the following determining peaks are: 274, 273, 146, 132 and 116.

Elemental analysis for · C

16 ^H 35 ° 2 ^N 'molecular weight 273 calculated: 70.33 wt. % carbon, 12.82 wt. % hydrogen, 5.13 wt. % nitrogen found: 70.27 wt. % carbon, 12.94 wt. % hydrogen, 5.07 wt. % nitrogen.

Example 4

The procedure is as in Example 1, except that 11 g (0.15 mol) of butylamine in 20 cm ^{3 of} ethanol are used. The yield is 84%, i.e. 24.1 g of 1-butylamino-3-decyloxy-2-propanol. The determining absorption bands on the infrared spectrum are the same as in Example 1. In the mass spectrum, the following determining peaks are: 288, 287, 160, 146 and 130. ·

Elemental analysis for C ₁₇ H ₇ O ₂ N, molecular weight 287 calculated: 71.08 wt. % carbon, 12.89 wt. % hydrogen, 4.88 wt. % nitrogen found: 70.89 wt. % carbon, 12.96 wt. % hydrogen, 4.81 wt. % nitrogen.

Example 5

The procedure is as in Example 1, except that 8.9 g (0.15 mol) of isopropylamine in 20 cm ^{3 of} ethanol are used. The yield is 82%, i.e. 22.4 g of 1-isopropylamino-3-decyloxy-2-propanol. The IR spectrum, said determining absorption bands: 3628, 3293, 2956, 2916, 2860, 2850, 1471, 1238, 1170, 1381, 1108, 1044, 723 cm ^- ^. In the mass spectrum, the following determining peaks are: 274, 273, 258, 146, 132 and 116.

Elemental analysis for GjHH ₃₃ O ₂ N, molecular weight 273 calculated: 70.33 wt. % carbon, 12.82 wt. % hydrogen, 5.13 wt. % nitrogen found: 70.24 wt. % carbon, 12.93 wt. % hydrogen, 5.05 wt. % nitrogen.

Example 6

The procedure is as in Example 1, except that 11 g (0.15 mol) of isobutyl3 are used.

amine in 20 cm 2 of ethanol. The yield is B5%, i.e. 24.4 g of 1-isobutylamino-3-decyloxy-2-propanol. The infrared spectrum was the same as in Example · 5. In the mass spectrum, the following determining peaks are: 288, 287, 272, 160, 146 and 130.

Elemental analysis for θ17 ^Η 37 ° 2 ^Ν 'molecular weight' 287 calculated: 71.08 wt. % carbon, 12.89 wt. % hydrogen, 4.88 wt. % nitrogen found: 70.92 wt. % carbon, 12.95 wt. % hydrogen, 4.84 wt. % nitrogen.

1-Alkylamino-3-decyloxy-2-propanols can find use as intermediates in the production of heterocyclic surfactants and detergents with antimicrobial effects.

Claims (1)

1-Alkylamino-3-decyloxy-2-propanols of the general formula I r-nh-ch ₂ -ch-ch ₂ -o- (ch ₂ ) ₉ -ch ₃ OH (1) wherein R represents methyl, ethyl, propyl, isopropyl, butyl and isobutyl.