1,1-dihaloalkane amine

Pyrrohdines also can be obtained by reaction of 1,4-dihydroxyaLkanes with amines in the presence of dehydrating agents at elevated temperatures or by reaction of primary amines with 1,4-dihaloaLkanes. The dry distillation of 1,4-butanediamine dihydrochloride also generates pyrrohdine. Pyrroles can also be catalyticahy hydrogenated to pyrrohdines. 

Several syntheses of l,3-dioxoperhydropyrrolo[l,2-c]imidazoles have been developed using different strategies. a-Substituted bicyclic proline hydantoins were prepared by alkylation of aldimines 135 of resin-bound amino acids with a,tu-dihaloalkanes and intramolecular displacement of the halide to generate cr-substituted prolines 136 and homologs (Scheme 18). After formation of resin-bound ureas 137 by reaction of these sterically hindered secondary amines with isocyanates, base-catalyzed cyclization/cleavage yielded the desired hydantoin products <2005TL3131>. 

Ethylenimines may also be prepared by the reaction of 1,2-dihaloalkanes with amines or ammonia. For example, ethylenimine may be prepared in the laboratory or on an industrial scale by the reaction of ethylene dichloride with ammonia [42]. The reaction of amines with a,/3-dibromo ketones yields imines as described in Eq. (18) [43]. 

Amines are generally too weak to effect a double dehydrohalogenation from dihaloalkanes. If, however, the hydrogens are made highly acidic by electronegative groups, elimination does take place (e.g. equation 65) . Recently it has been found... 

Terminal bis secondary amines can be cyclized with dihaloalkanes. There could be some template affect by alkali metal cations in the cyclization step even though the log K for the association of the alkali metal ions (except lithium) with a cyclic amine is low. In the building-block method to form the polyaza-crowns (methods 0-1 and 0-2), sodium, or potassium carbonate... 

Isoselenocyanates and selenoamides. Formamides are converted to isoseleno-cyanates by reaction with Se, EtjN, and phosgene in toluene. Selenoamides are obtained" from secondary amines, Se, and 1,1-dihaloalkanes in the presence of NaH in HMPA. An oxidation is involved. 

The synthesis of azetidines can be accomplished starting with r-substituted amines or 1,3-dihaloalkanes ... 

In the case of disecondary amines, of the procedures previously applied to the synthesis of N,N -diphenyl-a,(o-diaminoalkanes, the most widely used method has been the reaction of aniline with an a,(o-dihaloalkane in the presence of an alkali metal carbonate (57) or a large excess of aniline (10,11,24,26,51), However, this procedure frequently yields heterocyclic compounds as the principal products (8y9,12),... 

The DEAE-cottons containing from about 0.6% to 3.0% nitrogen in free amine form were washed free of -butanol with absolute methanol and then refluxed for about 5 hr in an ethanolic solution of about 10-20% of the alkyl halide or dihaloalkane. Treated fabrics were then washed in ethanol and dried. Storage was in t -butanol. 

Bis-nucleophilic 95, 97, 104 and bis-electrophilic 100 reagents are the result of the coupling of 4-amino-l,2,4-triazol-3(2T/)-thione derivatives, salicylic acid, and phenols with the dihaloalkanes and the derivatives of 2,3-dibromomethylquinoxaline 61 with the salicylaldehyde derivatives in various combinations. Changes in the combinations of the initial compounds allowed synthesis of the derivatives of bis(amines) 108 as the bis-nucleophilic reagent and the derivatives of bis(aldehydes) 109 as the bis-electrophilic reagent. 

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