1,3-propanediol amination

Diaminopropane Processes. 1,2-Propylenediamine can be produced by the reductive amination of propylene oxide (142), 1,2-propylene glycol [57-55-6] (143), or monoisopropanolamine [78-96-6] (144). 1,3-Propanediol [504-63-2] can be used to make 1,3-diaminopropane (143). Various propaneamines are produced by reducing the appropriate acrylonitrile—amine adducts (145—147). Polypropaneamines can be obtained by the oligomerization of 1,3-diaminopropane (148,149). 

A chain extender could be selected from the following compounds ethylene glycol, 1,2-propanediol, 1,4-butanediol, 1,3-butanediol, neopentanediol, hexanediol, methyl-dihydroxylethyl amine (MDEA) [9], etc. These should be as dry as possible. 

Among the amines that have been resolved with (-)-DAG are a-phenylethylamine (a-methylbenzenemethanamine),s [R-(R, R )]-2-amino-l-(4-nitrophenyl)-l, 3-propanediol,61,2,3,4,5,6,7,8-octahydro-l-(4-methoxyphenylmethyl)isoquinoline, 3-methoxymorphinan, 1,2,3,4-tetrahydro-7-methoxy-4-phenylisoquinoline, 3-hydroxy-A7-methyl-... 

A large number of nitramine-based explosives have been synthesized via Mannich-type condensation reactions (Section 5.13.2). The amines generated from these reactions often have the powerful electron-withdrawing trinitromethyl or fluorodinitromethyl groups positioned on the carbon a to the amino group. This reduces amine basicity to an extent that A-nitration becomes facile. The energetic nitramines (17), (19) and (21) have been synthesized from the condensation of ethylenediamine with 2,2,2-trinitroethanol, 2-fluoro-2,2-dinitroethanol with ethanolamine, and 2-fluoro-2,2-dinitroethylamine with 2,2-dinitro-l,3-propanediol respectively, followed by A-nitration of the resulting amine bases (16), (18) and (20), respectively. 

Another route to introduce the 1-[ F]fluoroisopropyl residue into the propanol-amine radioligands is represented by the model radiotracers listed in Table 3. [ F]Fluorometoprolol 6 exemplifies the less affine F-labeled counterpart of the )Si-AR-selective radioligand [ C]metoprolol [103]. 1-[ F]Fluoroisopropyl tosylate is the building block of choice used to prepare (+/ )-p F]fluorometopro-lol 6. 1-[ F]Fluoroisopropyl tosylate itself is accessible via the reaction of 1,2-propanediol di(p-toluenesulfonate) with [ F]K(Kryptofix 2.2.2)F. (+/ )-[ F]Fluorometoprolol 6 was proven to possess a similar Pt-AR selectivity like [ C]metoprolol, but its affinity appeared to be too low to potently visualize p-ARs in the heart with PET. 

Precursors for technological compounds 1,3-propanediol (DuPont) cyclic amino acids (Lonza) acrylamide (Nitto) (5)-l-methoxypropan-2-amine (CELGRO). 

Dinitroanil ino-trimethylolmethane N-(2,4-Dini trop henylamine)-trimethylolmeth-ane N (2,4-Dinitropkenyl)-(tris-hydroxy-metbyl-metbyl)-amine 2-(2, 4 -Dinitroanilino)-2-bydraxymethyl-1,3-propanediol 2,4-Di-nitropbenyltrimethylolmethylamine or 2,4-Dinitropbenyltrihydroxymethylmethylamine,... 

N-isopropylhydroxy 1 amine, AC18 2-methyl-2-hydroxamino-l,3 propanediol, AD53 2-methyl-2-hydroxami no-1-propanol, AD52... 

Amino-1,3-propanediol ( Glycerol-fi-mono-amine, /3-Aminotrimethyleneglycol, 2-Amino-... 

The use of oxetanes has been also explored. Both primary and secondary aliphatic amines react with oxetanes, under C02 (4MPa), at 373-393 K, in the absence of any catalyst, to afford monocarbamates of 1,3-propanediols, together with amino alcohols as side products [84]. 

At present, the most convenient way for the preparation of 1,3-disubstituted azetidines involves the alkylation of a primary amine with the bis-triflate of a 2-substituted 1,3-propanediol species in the presence of diisopropylethyl-amine <2006JOC7885>. 

Additives such as alcohols, phenols, and amines were used as received from Wako Chemical or Tokyo Chemical Industry, both in Japan. Maleic anhydride (MA) and phthalic anhydride (PA) were recrystallized from chloroform-hexane mixture and chloroform, respectively. 1,2-Propanediol (PG), styrene (St), and tetrahydrofuran (THF) were distilled before use. 

Chiral amino alcohols can be prepared by reaction of chiral epoxides with amines. Enantiopure (25, 3.R)-2,3-epoxy-3-phenylpropanol anchored to Merrifield resin has been used for ring-opening with secondary amines in the presence of lithium perchlorate to afford polymer-supported chiral amino alcohols 47 (Eq. 18) [56], By analogy, (2i ,35)-3-(cis-2,6-dimethylpiperidino)-3-phenyl-l,2-propanediol has been anchored to a 2-chlorotrityl chloride resin (48). Although this polymer had high catalytic activity in the enantioselective addition of diethylzinc to aldehydes, the selectivity of the corresponding monomeric catalyst was higher (97 % ee) in the same reaction. 

Amino-1,3 propanediol (G/ycero/ -wiono-amine, -Aminotrimethyleneglycol, 2-Am no-... 

See 1 -Nitro- 2-pc o py lam ino -2 -n itr amin oi m idazo 1-Idine and l-Nitro-2 propylamiho-2-imidazoline Nitrate under Aminoimidazoline and Amino-imidazolidine. Substituted Derivatives ywAminopropyleneglycol. See l-Amino-2,3 propanediol under Aminopropanediols... 

Glycerol-j8-mono amine. See 2-Amino 1,3-propanediol A251-L... 

C9H15N N,N-diallyl-2-propen-1 -amine 102-70-5 -73.15 1.0182 2 17990 C9H18N204 2-methyl-2-propyl-1,3-propanediol dicarbamate 57-53-4 25.00 1.1188 2... 

Reactivity is easily oxidized to benzoic acid through air oxidation. Reacts with alcohols to form acetals (e.g. ethanol, 1,2-propanediol) may form Schrff Bases with amines... 

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