Dimethylamine, reaction with alcohols

Substitution of an additional nitrogen atom onto the three-carbon side chain also serves to suppress tranquilizing activity at the expense of antispasmodic activity. Reaction of phenothia zine with epichlorohydrin by means of sodium hydride gives the epoxide 121. It should be noted that, even if initial attack in this reaction is on the epoxide, the alkoxide ion that would result from this nucleophilic addition can readily displace the adjacent chlorine to give the observed product. Opening of the oxirane with dimethylamine proceeds at the terminal position to afford the amino alcohol, 122. The amino alcohol is then converted to the halide (123). A displacement reaction with dimethylamine gives aminopromazine (124). ... 

Enantioselective conjugate addition of cuprates. This enantioselective reaction has been demonstrated using the amino alcohol 1, prepared by reaction of (2-chloroethyl)dimethylamine with(lR,2S)-(-)ephedrine, as a ligand.1 The cuprates obtained from 1 by deprotonation (RLi), reaction with CuI-S(CH,)2, and... 

Whereas l.l-dialkoxy-2.4.6-triphenyl-X -phosphorins do not show any nucleophilic substitution reactions, one of the alkoxy groups of the spiro compounds 192a and b can easily be substituted with alcohols by an alkoxy group in the presence of trifluoroacetic acid to 190. Treatment with dimethylamine in acidic me-... 

Betylates. Ammonioalkanesulfonate esters (1) have been given the trivial name betylates because they form betaines on substitution or elimination. They are prepared by reaction of alcohols with ethenesulfonyl chloride and trimethylamine and then with dimethylamine and CH3X. (equation I). ... 

Reacts with water or steam to produce heat. Violent reaction with bases (e.g., sodium hydroxide, potassium hydroxide, calcium hydroxide), alkali metals (e.g., sodium, potassium), amines (e.g., dimethylamine, triethylamine), lithium, pyridine. To fight fire, use alcohol foam. Incompatible with cations. When heated to decomposition (above 150°C) it emits acrid smoke and irritating fumes. See also ANHYDRIDES. 

Reacthity of chlorotropylium cations with nucleophiles. Alkuxy-, alkylthio-, and N-alkyl-N-arylaminotropylium. salts are prepared by reaction of chlorotropybum salts with alcohols, thiols, and N-alkyl-N-arylamines, respectively. With dimethylamine or with benzenesulfonamides chlorotropylium salts rearrange to yield bis(dimethyl-amino)phenylmethane or N-benzylidencsulfonamides. It is postulated that the formation of chlorocycloheptatrienes (IA, IB, 1C) is kinetically controlled, whereas substituted tropylium ions (3) are formed under thermodynamic control. 

Long-chain alcohols can be converted directly to A, A -dimethylalkyamines by the reaction with dimethylamine at 36°C in the presence of Th(S04)2 or in the presence of Cu-Cr catalyst and hydrogen at elevated temperamres and pressure (33, 34). 

It is produced from furfuryl alcohol by sequential reaction with dimethylamine hydrochloride/formaldehyde, cysteamine and N-methyl-l>(methylthio) 2-nitro-ethenamine. The production of ranitidine in 1986 amounted to 2601. 

Fatty alcohols are less commonly converted into intermediate alkyl halides through a reaction with POCI3, PCI3, or SOCI2, and then reacted with dimethylamine to form the tertiary amine. The resulting by-products include mixtures of phosphorous and phosphoric acids and their partially chlorinated forms that present handling and disposal challenges. 

In the second route, the fatty alcohol is first converted to the corresponding alkyl chloride by reaction with phosphorous trichloride or other chlorination agents. This alkyl chloride then reacts with dimethylamine to form the desired dimethylalkylamine [18] (Figure 20.11). 

A wide range of heteroatomic nucleophiles such as amines, alcohols and thiols have been shown to add to a-ferrocenylcarbenium ions. Carbon-carbon bond formation can also be achieved by addition of sUyl enol ethers. The following protocol involving the generation of a-ferrocenylethylium tetrafluoro-borate 13a and its subsequent reaction with dimethylamine is representative. 

Fatty alcohols are also available raw materials in the commercial preparation of tertiary amines. The fatty alcohol may be converted directly to an alkyl halide by the reaction with a concentrated hydrogen halide (2). The alkyl halide can then be reacted with dimethylamine to produce the tertiary amine (28). 

Direct conversion of fatty alcohols to primary amines by reaction with ammonia is not commercially practised but new catalyst developments show improved yields with this technology [10]. However, production of dialkylamines from alcohols is practised particularly with C8-C10 alcohols due to the limited availability of the corresponding acids. Alcohols are commonly used in the manufacture of tertiary alkyldimethylamines either through reductive amination with dimethylamine or by conversion to the alkylhaUde followed by reaction with dimethylamine. Both primary and secondary amines can be reacted with alcohols to produce tertiary trialkyl amines [11]. The chain branching seen with some synthetic alcohols means that the derived amines are not identical to those from natural sources. 

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