Morpholine pyrrolidine

The procedure is the same as that described in Chapter 9, Section T for the preparation of the morpholine enamine of cyclohexanone. In place of morpholine, pyrrolidine (12.8 g, 0.18 mole) is used. The product is collected at 114-115715 mm, 1.5200. 

Fig. 1 Schematic drawing showing the structure of tris(A/,AT-disubstituted-dithiocarbam-ato)iron(III). Substituents R1 and R2 represent various types of alkyl groups including those being part of the ring systems morpholine, pyrrolidine or pyrrole (Table 1)... 

Morpholine, pyrrolidine and sodium azide can also be also used as nucleophiles in the synthesis of 3-substitututed A3-cephems 515 via the conjugate addition of the 2,3-allenoate moiety in 513 [233]. 

In the reaction of 4-diazotriazoles with morpholine, pyrrolidine [83DIS(B)(43)2557], and several other secondary amines (66JMC733), the corresponding triazenes 247 were obtained. Also, in the case of 4-diazo-l,2,3-triazole-5-carboxamide, these compounds could easily be obtained in organic solvents despite the competing intramolecular ring closure to 2,8-diazahypoxanthine. In aqueous media, the intermolecular coupling... 

Success was obtained with Ru3(CO)i2 as catalyst precursor [6], but the most efficient catalysts were found in the RuCl2(arene)(phosphine) series. These complexes are known to produce ruthenium vinylidene spedes upon reaction with terminal alkynes under stoichiometric conditions, and thus are able to generate potential catalysts active for anti-Markovnikov addition [7]. Similar results were obtained by using Ru(r]" -cyclooctadiene)(ri -cyclooctatriene)/PR3 as catalyst precursor [8]. (Z)-Dienylcarba-mates were also regio- and stereo-selectively prepared from conjugated enynes and secondary aliphatic amines (diethylamine, piperidine, morpholine, pyrrolidine) but, in this case, RuCl2(arene) (phosphine) complexes were not very efficient and the best catalyst precursor was Ru(methallyl)2(diphenylphosphinoethane) [9] (Scheme 10.1). 

As commented above, gold(I) complexes with aliphatic amines are relatively unstable, but the use of disulfonylamides as counterions allows the synthesis of stable bis(amine)gold(I) cations [86]. Specifically, compounds with cyclohexylamine, benzylamine, 3-iodobenzylamine, morpholine, pyrrolidine, and piperidine as the amine ligands and bis(methanesulfonyl)amide, bis(p-chlorobenzenesulfonyl) amide, bis(p-iodobenzenesulfonyl)amide and o-benzenedisulfonylamide as the... 

Decarboxylation of malonic esters occurs in the presence of specific secondary amines, preferably, piperidine, morpholine, pyrrolidine, diethylamine or N-methylethanolamine (3). 

NR R = morpholine, pyrrolidine, piperidine, azepan-l-yl, NMej, NHBn... 

Dichloro- and trichloro-nitrobenzenes also react with Et2NH and cyclic amines (morpholine, pyrrolidine) at 0.6 GPa pressure to give mono-, di-, and trisubstitution products. For example, 2,3-dichloronitrobenzene (116a) and 2,5-dichloronitrobenzene (116b) reacted with these amines to give the... 

Enamines 10 (R,R, R = H,Me X = 0,S,NMe X = morpholine, pyrrolidine, piperidine) were prepared by reaction of the appropriate heterocyclic ketones with the heterocyclic base. ... 

The preparation of enamines ( )-RCH=CHNMe2 (R = substituted pyridyl) by the reaction of suitable substituted picolines, lutidines and collidines with Me2N(CHOMe)2 was described Treatment of secondary amines R2NH (morpholine, pyrrolidine, piperidine) with SOjClj gave N,N,JV, N -tetraalkylsulphinyldiamines, which subsequently underwent dehydration in the presence of aldehydes and ketones to give enamines in good yields ... 

T he exchange of the chloro substituents in the pyridazine part of substituted 1,4-dichloropyri-do[3,4-fi ]pyridazines by reaction with cyclic amines, such as morpholine, substituted morpholines, pyrrolidine, and piperidine at reflux temperature gives products 12.119,121,135,138 The crude dichloro compound may be used.119... 

In a comparable way 2-aminophenols can be prepared in variable yields from 2-acylfuranones and a cyclic amine, such as piperidine in the example given, although morpholine pyrrolidine served equally well (ref.94). These phenolic structures are now accessible by more well-known methods. 

Piperidine, morpholine, pyrrolidine, N-alkylpiperazines, and anilines have been converted to N-aryl derivatives by use of aryl triflates under the action of microwave irradiation in NMP [58]. The amination reaction proceeded efEciently in the absence of base and catalyst, and was not affected by traces of water (Scheme 10.23). 

On the other hand, reaction of the sulfonyl chloride 397 with excess morpholine, pyrrolidine and piperidine (three equivalents) afforded a mixture of the sulfonamides 400 and 401. The succinimidosulfonamide 401 was formed by simultaneous nucleophilic substitution at sulfur and Michael addition of the amine to the activated alkenic double bond. The pure maleimidosulfonamide 400 could be prepared by column chromatography of the mixture. The reaction of N- p-chlorosulfonylphenyl) maleimide 397 with excess dimethylamine or diethylamine in methanol as solvent resulted in the formation of ring-opened products. For instance, in the reaction with diethylamine, the methyl ester 402 was formed by base-catalysed nucleophilic ring-opening by the solvent (methanol) this ring... 

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