2- Dimethylaminoethyl chloride

Cationic Starches. The two general categories of commercial cationic starches are tertiary and quaternary aminoalkyl ethers. Tertiary aminoalkyl ethers are prepared by treating an alkaline starch dispersion with a tertiary amine containing a P-halogenated alkyl, 3-chloto-2-hydtoxyptopyl radical, or a 2,3-epoxypropyl group. Under these reaction conditions, starch ethers are formed that contain tertiary amine free bases. Treatment with acid easily produces the cationic form. Amines used in this reaction include 2-dimethylaminoethyl chloride, 2-diethylaminoethyl chloride, and A/-(2,3-epoxypropyl) diethylamine. Commercial preparation of low DS derivatives employ reaction times of 6—12 h at 40—45°C for complete reaction. The final product is filtered, washed, and dried. 

Further substitution of benzoic acid leads to a drug with antiemetic activity. Alkylation of the sodium salt of p-hydroxy-benzaldehyde (8) with 2-dimethylaminoethyl chloride affords the so-called basic ether (9). Reductive amination of the aldehyde in the presence of ammonia gives diamine, 10. Acylation of that product with 3,4,5-trimethoxybenzoyl chloride affords trimetho-benzamide (11). ... 

Alkylation of 1-indanone with 2-dimethylaminoethyl chloride affords the substituted ketone (1). Condensation with the lithium reagent obtained from 2-ethylpyridine affords the alcohol (2). Dehydration under acidic conditions gives dimethyl-pyrindene (3). ... 

An alternate scheme for preparation of the last drug involves first bromination of the methylene group on 33 (obtainable by several methods from 27). A displacement reaction of the Grignard reagent prepared from 34 on 2-dimethylaminoethyl chloride affords again amytriptylene (32). ... 

Nucleophilic aromatic substitution of the anthranilic acid derivatives, 72, on ortho-bromonitrobenzene affords the diphenyl-amine, 73. The ester is then saponified and the nitro group reduced to the amine (74). Cyclization of the resulting amino acid by heat affords the lactam (75). Alkylation on the amide nitrogen with 2-dimethylaminoethyl chloride by means of sodium amide affords dibenzepine (76). ... 

The low structural specificity of the antihistamines has already been noted. It is perhaps not too surprising, therefore, to find Lhat attachment of the basic side chain directly onto one of the. iromatic rings affords active compounds. In an unusual reaction reminiscent of the Claisen rearrangement, benzyl chloride affords the substituted phenol, 46, on heating with phenol itself. Alkyl-.ition of 46 with 2-dimethylaminoethyl chloride gives phenyltolox-.imine (47).Alkylation of that same intermediate (46) with 1-bromo-2-chloropropane, leads to 48. Use of that halide to alkyl-,ite piperidine gives the antihistamine, pirexyl (49). ... 

I ollowed by acylation gives the acetamide, S3. Alkylation of the phenol with 2-dimethylaminoethyl chloride gives the corresponding basic ether (S4). Hydrolysis of the amide gives the free... 

A solution of 219 g (1 mol) of a-(p-chlorophenyl)-2-pyridinemethanol in one liter of dry toluene is heated to 100°C with stirring. Twenty-three grams (1 g-atom) of sodium are then added in portions. After all the sodium has reacted, a dried solution of 2-dimethylaminoethyl chloride in benzene is added. This benzene solution is prepared by dissolving 173 g (1.2 mols) of 2-dimethylaminoethyl chloride hydrochloride in the minimum amount of water, adding 500 cc of benzene followed by 300 g of sodium carbonate decahydrate, stirring, separating the benzene layer and drying. 

To 122 grams (1 mol) of p-hydroxybenzaldehyde in 1 liter of chlorobenzene were added 66 grams (1.04 mols) of sodium methoxide (85%) and 108 grams (1 mol) of 2-dimethylaminoethyl chloride. The mixture was stirred and refluxed for 15 hours, then cooled and the precipitated sodium chloride filtered off. The filtrate was concentrated at steam temperature under water vacuum and the residual oil was fractionated in high vacuum, to give 4-(2-dimethylaminoethoxy)benzaldehyde, BP2.2145°C. 

A suspension of 30 g of sodium hydride in benzene (30 ml) was added dropwise to 52 g of 8-chlorodibenzo[b,f]thiepin-10(llH)-one dissolved in dimethylformamide (800 ml), and the mixture was heated at 100°C for 2 hours. To this, there were added 68 g of 2-dimethylaminoethyl chloride, and the mixture was heated at 60°C for 39 hours. The reaction mixture, after cooled, was poured into ice-water, and the solution was extracted with ethyl acetate. The ethyl acetate layer, after washed with water, was extracted with 10% hydrochloric acid, when oil was precipitated. The aqueous layer, in which oil was precipitated, was washed with ether, made neutral with concentrated sodium hydroxide solution and then extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over magnesium sulfate, and concentrated to give oil, which was allowed to stand to provide solid. The solid was washed with petroleum ether and recrystallized from cyclohexane to yield 42.5 g of 8-chloro-10-(2-dimethylaminoethyl)-oxydibenzo[b,f]thiepin as crystals, melting point 90°C to 91°C. Maleate as colorless needle, melting point 204°C to 204.5°C. 

A mixture of 22.5 g 4-nitro-2-/i-propoxy benzoic acid (0.10 mol), 11.0 g KHCO3, and 400 mL dry toluene was stirred and refluxed under a water trap until dehydration was complete ( 2 h). The water trap was removed, and 12.9 g 2-dimethylaminoethyl chloride (0.12 mol) was added. Stirring and refluxing were continued for 20 h. The mixture was filtered while hot, and the filter cake was washed well with hot toluene. The toluene was removed from the combined filtrates in vacuo and the residual oil was dissolved in dilute hydrochloric acid. After decolorization, the solution was treated with solid K2CO3, and the liberated base was taken up in EtOAc. After drying over Drierite, EtOAc was evaporated in vacuo and 24.0 g 2-dimethylaminoethyl 4-nitro-2-n-propoxy benzoate was obtained as oil, in a yield of 81%. 

Dimethylaminoethyl chloride hydrochloride. See Dimethylaminoethyl chloride hydrochloride... 

In the presence of sodamide, 2-picoline or 2-benzylpyridine condenses with 2-dimethylaminoethyl chloride to give l-(2-pyridyl)-3-dimethyIaminopropane (IX-245, R l-phenyl-l-(2-pyridyl)-3-dimethylaminopropane (IX-24S, R = CfiHs), respectively. - ... 

A slight excess of 2-dimethylaminoethyl chloride added to a soln. of Na-1-phenylcyclohexoxide in toluene, and refluxed 1-3 hrs. with stirring 1-phenyl-cyclohexyl 2-dimethylaminoethyl ether. Y 75%.—y-, and d-Halogenamines give aminoethers whereas prim, alkyl halides form ethylene derivatives with elimination of hydrogen halide under the above conditions. F. e. s. B. Tchoubar and M. Verrier, Bl. 1960, 2151. 

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