3 Dimethylaminoethanol

Chemical Name 4-(acetylamino)benzoic acid compound with 2-(dimethylaminoethanol)... 

Dimethylaminoethanol (DMAE), also known as N,N-dimethylethanolamine (DMEA) HOCH2CH2N(CH3)2 MW = 89.1. Sp.gr. = 0.887. Flash point = 105 °F/40 °C. Available as a 98.5+% amine commodity product from various international manufacturers and commonly available through chemical distributors. 

Cervinka and co-workers have extensively investigated the asymmetric reduction of prochiral ketones with LAH modified with alkaloids and related amino alcohols. Most of this work has been reviewed in detail by Morrison and Mosher (1) and will not be discussed extensively here. Modification of LAH was effected with (-)-quinine (65), (- )-cinchonidine (66), (- )-ephedrine (67), (-)-A-ethyl-ephedrine (68), (-)- l-phenyl-2-dimethylaminoethanol (69), (+ )-quinidine (70), (+ )-cinchonine (71), and (+ )-pseudoephedrine (72). 

Diphenhydramine Diphenhydramine, 2-diphenylmethoxy-iVA -dimethylamine (10.2.5), is synthesized by the esterification of 2-dimethylaminoethanol with benzhydrylbrotnide [35-37],... 

Succinylcholine Succinylcholine, 2,2 -[(l,4-dioxo-l,4-butanediyl)fcw(oxy)]few[Af,Af,Af-trimethylethanaminium(diacetylcholine)] dichloride, which can be viewed as a dimeric molecule of acetylcholine (diacetylcholine), is synthesized by reacting succinic acid dichloride with 2-dimethylaminoethanol and subsequent transformation of the resulting bM-(2-dimethy-laminoethyl)succinate (15.1.13) into a quaternary salt, succinylcholine (15.1.14) [20-24]. 

Diphenhydramine Diphenhydramine, A,A-dimethyl-(diphenylmethoxy)ethylamine (16.1.1), is synthesized by a simple reaction of benzhydrylbromide and 2-dimethylaminoethanol [1-3]. 

Dimethylaminoethanol and derivs 5 D1310 2-dimethylaminoethanol nitrate 5 D1310... 

Tetramethoxysilane (abbreviated as TMOS) and octadecyltrimethyl-ammonium chloride [(C18H37)(CH3)3N+Cr abbreviated as C18TAC] were obtained from Tokyo Kasei Industries Co., and used without further purification. A cationic azobenezene derivative [abbreviated as AZ] (the molecular structure is shown in Scheme 11) was prepared by the reaction between 4-phenylazophenol, 1,2-dibromoethane, and 2-dimethylaminoethanol, obtained from Tokyo Kasei Industries Co. 

Other coordination modes in pseudohalide complexes are comparatively rare. Amongst them, we note the structure of complex [AgLSCN] 0.25L (L = bipy), in which two silver ions are simultaneously bound with N atoms from NCS groups [166], The pseudohalide complexes with simultaneous different kinds of coordination of the NCS group are also rare. In particular, the complex compound [CuL(HL)2][Cu(L)(SCN)(p-NCS)], where LH is 2-dimethylaminoethanol, contains within its coordination sphere both kinds S-terminal (108) and -bridge (109) thiocyanate groups [178],... 

At the same time, a transformation, similar to (3.272), with participation of ethyle-nediamine (en), PbO, NH4SCN, and 2-dimethylaminoethanol is accompanied by the formation (82%) of structurally characterized trinuclear complex Pb3(en)6(SCN)6 [678],... 

A solution of 21.7 g (0.11 mole) 1-adamantanecarboxylic acid chloride in 100 ml ether was added to a solution of 19.4 g (0.22 mole) 2-dimethylaminoethanol in 200 ml ether. The reaction mixture was stirred overnight at room temperature. Then additional 15.0 g (0.17 mole) 2-dimethylaminoethanol was added and the reaction mixture again stirred overnight. The reaction mixture was poured into 300 ml water and treated with 20 ml of 10% NaOH solution. From the ether layer was recovered 23.0 g of 2-dimethylaminoethyl 1-adamantanecarboxylate as oil. 

The crude product (48.4 grams, 80.9% yield) was recrystallized from an absolute ethanol-ethyl acetate solvent system by suspending the salt in boiling anhydrous ethyl acetate and just enough absolute ethanol was gradually added to effect solution after which the solution was concentrated to about two-thirds of the original volume on the steam bath, charcoal treated, and suction-filtered through Celite filter aid. The white crystals of 2-dimethylaminoethanol p-acetylaminobenzoate obtained, dried at room temperature at a pressure of 0.08 mm Hg for 15 hours, melted at 159.0°-161.5°C. 

A 116 parts by weight of phenyl-p-methoxy-chloromethane (4-methoxybenzhydryl chloride) were added to 500 parts by weight of toluene and to the resulting mixture 65 parts by weight of 2-dimethylaminoethanol was added. Then the entire mixture was refluxed for two hours. The refluxed mixture was cooled and 250 parts by weight of a 10% solution of sodium hydroxide were added. This alkaline mixture was then steam distilled until the distillate was only weakly alkaline, for example a pH 7.5-8. 

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