1-(2-aminoethylamino)ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-[2-(2-hydroxyethyl)aminoethyl]octadecanamide and N-[2-(2-hydroxyethyl)aminoethyl]pentanamide have been obtained as hydrolysis products from the corresponding imidazolines by Harnsberger and Riebsomer, J. Hetero. Chem. 1, 188 (1964); Gabriel, J. Amer. Oil Chem. Soc., 61, 965 (1984), has described the formation of N-(2-aminoethyl)-N-(2-hydroxyethyl)dodecanamide and N-[2-(2-hydroxyethyl)aminoethyl]dodecanamide as kinetically and thermodynamically controlled products respectively from reaction of N-(2-aminoethyl)aminoethanol and methyl laurate in the presence of catalytic amount of sodium methoxide; Horibatake et al., Jpn. Kokai Tokkyo Koho JP 62,132,946, 16 Jun 1987; C.A. 108, 22881p (1988) claim acylaminoalkyl aminoalkanols, for example, N-[2-(2-hydroxy- ethyl)aminoethyl]dodecanamide, as antistatic agents for synthetic resins; Higuchi and Takahashi, Jpn. Kokai Tokkyo Koho JP 62 57,491, 13 Mar. 1987; C.A. 107, 178711y (1987) claim N-[2-(2-hydroxyethyl) aminoethyl]dodecanamide as being essential in a detergent composition useful for cleaning machines; Moriguchi, Jpn. Kokai Tokkyo Koho JP 62,104,842, 15 May 1987; C.A. 107, 177783m (1987) mentions compositions containing acylaminoalkyleneamines and aminoalcohols as antitack agents for unvulcanized rubbers; Higuchi and Takahashi, Jpn. Kokai Tokkyo Koho JP 61,114,726, 02 Jun 1986; C.A. 105, 155513e (1986) mention the use of N-[2-(2-hydroxyethyl) aminoethyl]dodecanamide and octadec-9-enamide and N-(2-aminoethyl)-N-(2-hydroxyethyl)dodecanamide as emulsifying agents for stable emulsions; Moriguchi, Jpn. Kokai Tokyo Koho JP 71 09,939, 13 Mar 1971; C.A. 76, 60500s (1972) describe the use of N-[2-(2-Hydroxyethyl)aminoethyl]dodecanamide and octadecanamide as heat and water resistant antistatic agents; N-2-aminoethylamides of lower carboxylic acids have been reported by Rosenmund, U.S. Pat. No. 1,926,015 (Sep. 5, 1933); dodecanoic and tetradecanoic acid derivatives (m.p. 51°-2° C. and 62° C.) have been synthesized by Weiner, U.S. Pat. No. 2,387,201 (Oct. 16, 1945) and the latter (m.p. 150°-152° C.) by Kyrides, U.S. Pat. No. 2,399,601 (Apr. 30, 1946), but purity of these compounds is questionable based on the discrepancy in the reported melting points; Harnsberger and Riebsomer have isolated N-[2-(2-hydroxyethyl)aminoethyl]octadecanamide and pentanamide as hydrolysis products from the corresponding imidazolines. as heat

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-[2-(2-hydroxyethyl)aminoethyl]octadecanamide and N-[2-(2-hydroxyethyl)aminoethyl]pentanamide have been obtained as hydrolysis products from the corresponding imidazolines by Harnsberger and Riebsomer, J. Hetero. Chem. 1, 188 (1964); Gabriel, J. Amer. Oil Chem. Soc., 61, 965 (1984), has described the formation of N-(2-aminoethyl)-N-(2-hydroxyethyl)dodecanamide and N-[2-(2-hydroxyethyl)aminoethyl]dodecanamide as kinetically and thermodynamically controlled products respectively from reaction of N-(2-aminoethyl)aminoethanol and methyl laurate in the presence of catalytic amount of sodium methoxide; Horibatake et al., Jpn. Kokai Tokkyo Koho JP 62,132,946, 16 Jun 1987; C.A. 108, 22881p (1988) claim acylaminoalkyl aminoalkanols, for example, N-[2-(2-hydroxy- ethyl)aminoethyl]dodecanamide, as antistatic agents for synthetic resins; Higuchi and Takahashi, Jpn. Kokai Tokkyo Koho JP 62 57,491, 13 Mar. 1987; C.A. 107, 178711y (1987) claim N-[2-(2-hydroxyethyl) aminoethyl]dodecanamide as being essential in a detergent composition useful for cleaning machines; Moriguchi, Jpn. Kokai Tokkyo Koho JP 62,104,842, 15 May 1987; C.A. 107, 177783m (1987) mentions compositions containing acylaminoalkyleneamines and aminoalcohols as antitack agents for unvulcanized rubbers; Higuchi and Takahashi, Jpn. Kokai Tokkyo Koho JP 61,114,726, 02 Jun 1986; C.A. 105, 155513e (1986) mention the use of N-[2-(2-hydroxyethyl) aminoethyl]dodecanamide and octadec-9-enamide and N-(2-aminoethyl)-N-(2-hydroxyethyl)dodecanamide as emulsifying agents for stable emulsions; Moriguchi, Jpn. Kokai Tokyo Koho JP 71 09,939, 13 Mar 1971; C.A. 76, 60500s (1972) describe the use of N-[2-(2-Hydroxyethyl)aminoethyl]dodecanamide and octadecanamide as heat and water resistant antistatic agents; N-2-aminoethylamides of lower carboxylic acids have been reported by Rosenmund, U.S. Pat. No. 1,926,015 (Sep. 5, 1933); dodecanoic and tetradecanoic acid derivatives (m.p. 51°-2° C. and 62° C.) have been synthesized by Weiner, U.S. Pat. No. 2,387,201 (Oct. 16, 1945) and the latter (m.p. 150°-152° C.) by Kyrides, U.S. Pat. No. 2,399,601 (Apr. 30, 1946), but purity of these compounds is questionable based on the discrepancy in the reported melting points; Harnsberger and Riebsomer have isolated N-[2-(2-hydroxyethyl)aminoethyl]octadecanamide and pentanamide as hydrolysis products from the corresponding imidazolines. as heat

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-[2-(2-hydroxyethyl)aminoethyl]octadecanamide and N-[2-(2-hydroxyethyl)aminoethyl]pentanamide have been obtained as hydrolysis products from the corresponding imidazolines by Harnsberger and Riebsomer, J. Hetero. Chem. 1, 188 (1964); Gabriel, J. Amer. Oil Chem. Soc., 61, 965 (1984), has described the formation of N-(2-aminoethyl)-N-(2-hydroxyethyl)dodecanamide and N-[2-(2-hydroxyethyl)aminoethyl]dodecanamide as kinetically and thermodynamically controlled products respectively from reaction of N-(2-aminoethyl)aminoethanol and methyl laurate in the presence of catalytic amount of sodium methoxide; Horibatake et al., Jpn. Kokai Tokkyo Koho JP 62,132,946, 16 Jun 1987; C.A. 108, 22881p (1988) claim acylaminoalkyl aminoalkanols, for example, N-[2-(2-hydroxy- ethyl)aminoethyl]dodecanamide, as antistatic agents for synthetic resins; Higuchi and Takahashi, Jpn. Kokai Tokkyo Koho JP 62 57,491, 13 Mar. 1987; C.A. 107, 178711y (1987) claim N-[2-(2-hydroxyethyl) aminoethyl]dodecanamide as being essential in a detergent composition useful for cleaning machines; Moriguchi, Jpn. Kokai Tokkyo Koho JP 62,104,842, 15 May 1987; C.A. 107, 177783m (1987) mentions compositions containing acylaminoalkyleneamines and aminoalcohols as antitack agents for unvulcanized rubbers; Higuchi and Takahashi, Jpn. Kokai Tokkyo Koho JP 61,114,726, 02 Jun 1986; C.A. 105, 155513e (1986) mention the use of N-[2-(2-hydroxyethyl) aminoethyl]dodecanamide and octadec-9-enamide and N-(2-aminoethyl)-N-(2-hydroxyethyl)dodecanamide as emulsifying agents for stable emulsions; Moriguchi, Jpn. Kokai Tokyo Koho JP 71 09,939, 13 Mar 1971; C.A. 76, 60500s (1972) describe the use of N-[2-(2-Hydroxyethyl)aminoethyl]dodecanamide and octadecanamide as heat and water resistant antistatic agents; N-2-aminoethylamides of lower carboxylic acids have been reported by Rosenmund, U.S. Pat. No. 1,926,015 (Sep. 5, 1933); dodecanoic and tetradecanoic acid derivatives (m.p. 51°-2° C. and 62° C.) have been synthesized by Weiner, U.S. Pat. No. 2,387,201 (Oct. 16, 1945) and the latter (m.p. 150°-152° C.) by Kyrides, U.S. Pat. No. 2,399,601 (Apr. 30, 1946), but purity of these compounds is questionable based on the discrepancy in the reported melting points; Harnsberger and Riebsomer have isolated N-[2-(2-hydroxyethyl)aminoethyl]octadecanamide and pentanamide as hydrolysis products from the corresponding imidazolines. as heat

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 30-ml two-necked flask equipped with a stirrer and dropping funnel was charged with 2.08 g (20 mmol) of aminoethylaminoethanol and 0.054 g (1 mmol) of sodium methoxide. While heating and stirring the contents at 80° C. in an N2 atmosphere, a solution of 3.29 g (10 mmol) of ethyl 12-hydroxystearate in 10 ml of THF was added dropwise over 2 hours. The resultant mixture was stirred further for 13 hours at 80° C. under reduced pressure. After completion of the reaction, the reaction mixture was poured into 500 ml of water, and precipitate formed was purified by flash column chromatography on silica gel, thereby obtaining 2.85 g (yield: 74%) of the title compound (IIf-1). A 30-ml two-necked flask equipped with a stirrer While heating After completion of the reaction formed was purified by flash column chromatography on silica gel

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 30-ml two-necked flask equipped with a stirrer and dropping funnel was charged with 2.08 g (20 mmol) of aminoethylaminoethanol and 0.054 g (1 mmol) of sodium methoxide. While heating and stirring the contents at 80° C. in an N2 atmosphere, a solution of 3.29 g (10 mmol) of ethyl 12-hydroxystearate in 10 ml of THF was added dropwise over 2 hours. The resultant mixture was stirred further for 13 hours at 80° C. under reduced pressure. After completion of the reaction, the reaction mixture was poured into 500 ml of water, and precipitate formed was purified by flash column chromatography on silica gel, thereby obtaining 2.85 g (yield: 74%) of the title compound (IIf-1). A 30-ml two-necked flask equipped with a stirrer While heating After completion of the reaction formed was purified by flash column chromatography on silica gel

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-[2-(2-hydroxyethyl)aminoethyl]octadecanamide and N-[2-(2-hydroxyethyl)aminoethyl]pentanamide have been obtained as hydrolysis products from the corresponding imidazolines by Harnsberger and Riebsomer, J. Hetero. Chem. 1, 188 (1964); Gabriel, J. Amer. Oil Chem. Soc., 61, 965 (1984), has described the formation of N-(2-aminoethyl)-N-(2-hydroxyethyl)dodecanamide and N-[2-(2-hydroxyethyl)aminoethyl]dodecanamide as kinetically and thermodynamically controlled products respectively from reaction of N-(2-aminoethyl)aminoethanol and methyl laurate in the presence of catalytic amount of sodium methoxide; Horibatake et al., Jpn. Kokai Tokkyo Koho JP 62,132,946, 16 Jun 1987; C.A. 108, 22881p (1988) claim acylaminoalkyl aminoalkanols, for example, N-[2-(2-hydroxy- ethyl)aminoethyl]dodecanamide, as antistatic agents for synthetic resins; Higuchi and Takahashi, Jpn. Kokai Tokkyo Koho JP 62 57,491, 13 Mar. 1987; C.A. 107, 178711y (1987) claim N-[2-(2-hydroxyethyl) aminoethyl]dodecanamide as being essential in a detergent composition useful for cleaning machines; Moriguchi, Jpn. Kokai Tokkyo Koho JP 62,104,842, 15 May 1987; C.A. 107, 177783m (1987) mentions compositions containing acylaminoalkyleneamines and aminoalcohols as antitack agents for unvulcanized rubbers; Higuchi and Takahashi, Jpn. Kokai Tokkyo Koho JP 61,114,726, 02 Jun 1986; C.A. 105, 155513e (1986) mention the use of N-[2-(2-hydroxyethyl) aminoethyl]dodecanamide and octadec-9-enamide and N-(2-aminoethyl)-N-(2-hydroxyethyl)dodecanamide as emulsifying agents for stable emulsions; Moriguchi, Jpn. Kokai Tokyo Koho JP 71 09,939, 13 Mar 1971; C.A. 76, 60500s (1972) describe the use of N-[2-(2-Hydroxyethyl)aminoethyl]dodecanamide and octadecanamide as heat and water resistant antistatic agents; N-2-aminoethylamides of lower carboxylic acids have been reported by Rosenmund, U.S. Pat. No. 1,926,015 (Sep. 5, 1933); dodecanoic and tetradecanoic acid derivatives (m.p. 51°-2° C. and 62° C.) have been synthesized by Weiner, U.S. Pat. No. 2,387,201 (Oct. 16, 1945) and the latter (m.p. 150°-152° C.) by Kyrides, U.S. Pat. No. 2,399,601 (Apr. 30, 1946), but purity of these compounds is questionable based on the discrepancy in the reported melting points; Harnsberger and Riebsomer have isolated N-[2-(2-hydroxyethyl)aminoethyl]octadecanamide and pentanamide as hydrolysis products from the corresponding imidazolines. as heat

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 30-ml two-necked flask equipped with a stirrer and dropping funnel was charged with 2.08 g (20 mmol) of aminoethylaminoethanol and 0.054 g (1 mmol) of sodium methoxide. While heating and stirring the contents at 80° C. in an N2 atmosphere, a solution of 3.29 g (10 mmol) of ethyl 12-hydroxystearate in 10 ml of THF was added dropwise over 2 hours. The resultant mixture was stirred further for 13 hours at 80° C. under reduced pressure. After completion of the reaction, the reaction mixture was poured into 500 ml of water, and precipitate formed was purified by flash column chromatography on silica gel, thereby obtaining 2.85 g (yield: 74%) of the title compound (IIf-1). A 30-ml two-necked flask equipped with a stirrer While heating After completion of the reaction formed was purified by flash column chromatography on silica gel