Dimethylaminopropyl amine

Cocamidopropyl betaine is manufactured by a two-step reaction coconut oil-derived fatty acid is reacted with dimethylaminopropyl-amine to yield the cocamide that is subsequently converted to the betaine by the addition of monochloroacetate. The acyl group in the amide linkage ranges in length from 8 to 16 carbon atoms with C12 and C14 as the predominant components [44]. 

Weak Base Functionality. Amination with dimethylaminopropyl-amine (DMAPA) introduces a tertiary amine functional group. 

Halogen atoms activated by carbonyl groups adjacent to the benzene ring can be, in some cases, displaced with nucleophiles. For example, compound (250) treated with iV,A(-dimethylaminopropyl amine gives the product of monosubstitution (251) together with the rearrangement 2 1 product (252). No product of normal disubstitution is formed (Equation (34)) <92CPB2905>. 

The first example in Table 2.5 was made from a partly epoxidized butadiene resin by reaction with dimethylamine followed by acrylic acid. The second example was again a reaction product of polybutadiene with maleic acid, followed by treatment with N,N-dimethylaminopropyl-amine. This polyamine was mixed with a novolac resin containing sites of unsaturation, an example of which is shown in Fig. 2.10. 

Chem. Descrip. Coconut oil dimethylaminopropyl amine condensate Uses Raw material for prod, of coconut amine oxide surfactants CDO-600 [NikkoChems.Co.Ltd]... 

Strong bases, such as potassium acetate, potassium 2-ethylhexoate, or amine—epoxide combinations are the most useful trimerization catalysts. Also, some special tertiary amines, such as 2,4,6-tns(A7,A7-dimethylarninomethyl)phenol (DMT-30) (6), l,3,5-tris(3-dimethylaminopropyl)hexahydro-j -triazine (7), and ammonium salts (Dabco TMR) (8) are good trimerization catalysts. 

Indazoles can be considered as either azaindoles or azaisoindoles depending on the reader s prejudice. Benzydamine (54) represents a drug with this heterocyclic nucleus. Alkylation of the amine of anthranilic acid methyl ester with benzyl chloride in the presence of sodium acetate gives 52. Treatment with nitrous acid leads to the nitrosoamine, which cyclizes spontaneously to the 3-ketoindazole system, 53. This intermediate forms an ether of its enol form on heating the sodium salt with 3-dimethylaminopropyl chloride. There is thus obtained benzydamine (54), a fairly potent nonsteroidal antiinflammatory agent with significant antipyretic and analgesic properties. 

Ullmann condensation of the sodium salt of p-chlorothiophe-nol (31) with 2-iodobenzoic (32) acid gives 33. Cyclization by means of sulfuric acid affords the thioxanthone, 34. Reaction with the Grignard reagent from 3-dimethylaminopropyl chloride affords the tertiary carbinol (35). Dehydration by means of acetic anhydride affords chlorprothixene as a mixture of geometric isomers, 36. (Subsequent work showed the Z isomer-chlorine and amine on the same side—to be the more potent compound.) Chlorprothixene is said to cause less sedation than the phenothiazines. ... 

The reactions involved in an EDC-mediated conjugation are discussed in Chapter 3, Section 1.1 (Note EDC is l-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride MW 191.7 and is sometimes referred to as EDAC). The carbodiimide first reacts with available carboxylic groups on either the carrier or hapten to form a highly reactive o-acylisourea intermediate. The activated carboxylic group then can react with a primary amine to form an amide bond, with release of the EDC mediator as a soluble isourea derivative. The reaction is quite efficient with no more than 2 hours required for it to go to completion and form a conjugated immunogen. 

The best results were achieved by employing N-(3-dimethylaminopropyl)-N -ethylcar-bodiimide hydrochloride (EDC) as coupling agent. After Fmoc deprotection with piperidine in N,N-dimethylformamide, additional diversity could be introduced by acylation of the liberated amine position. Finally, the acyl cyano phosphoranes could be efficiently cleaved by ozonolysis at -78 °C or by utilizing freshly distilled 3,3-dimethyloxirane at room temperature [65]. The released compounds constituted highly activated electrophiles, which could be further converted in situ with appropriate nucleophiles. 

The spacer arm length between the hapten and the carrier is in the range of 6 to 8 A, which should eliminate any steric interference with carrier side chains. According to the protocol described by Schultz the haptens were coupled to BSA and KLH via A-(3-dimethylaminopropyl)-A -ethylcarbodiimide or the N-hydroxysuccinimide ester at pH 5.5 in water. Other coupling strategies include substitution with diazonium salts and reductive amination. The ratio of hapten-carrier range between 8 and 15 haptens per carrier. 

Coupling the substituents to the polyacid core is a key step. The reaction must have a high yield to limit purification problems and show high selectivity between the amines and alcohols present to limit side reactions. The amidifica-tion reaction chosen is a coupling reaction used in peptide chemistry. The reaction is carried out at room temperature in the presence of a coupling reagent such as NjAT -dicyclohexylcarbodiimide, l-(3-dimethylaminopropyl)-3-ethylcar-bodiimide or l-ethoxycarbonyl-2-ethoxyl-l,2-dihydroquinoline, possibly in the presence of an activator such as hydroxybenzotriazole or N-hydroxysuccimide (Fig. 8). 

The carbodiimide of choice used to couple cystamine to carboxylate- or phosphate-containing molecules is most often the water-soluble carbodiimide EDC (l-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride Chapter 3, Section 1.1). This reagent rapidly reacts with carboxylates or phosphates to form an active complex highly reactive toward primary amines. The reaction is efficient from pH 4.7 to 7.5, and a variety of buffers may be used, providing they do not contain competing groups. 

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