241  US 9,323,153 B2  242  (2) Compound Having a Nitrogen-Containing Heterocycle  Structure  A nitrogen-containing heterocycle may have aromatic  properties or may not have aromatic properties. Further, it  may have a plurality of nitrogen atoms. Also it may have a  heteroatom other than nitrogen. Specifically, examples  thereof include compounds having an imidazole structure  (2-phenylbenzoimidazole, 2,4,5-triphenylimidazole, and the  like), compounds having a piperidine structure (N-hydroxy› ethylpiperidine,  bis( 1,2,2,6,6-pentamethy 1-4-piperidyl)  sebacate, and the like), compounds having a pyridine struc› ture ( 4-dimethylaminopyridine and the like), and compounds  having an antipyrine structure (antipyrine, hydroxyantipy› rine, and the like).  In addition, compounds with two or more ring structures  can be appropriately used. Specific examples thereof include  1,5-diazabicyclo[4.3.0]non-5-ene  and  1,8-diazabicyclo  [5.4.0]-undec-7-ene.  (3) Amine Compound Having a Phenoxy Group  The amine compounds containing a phenoxy group are  those having a phenoxy group at the end opposite to the  nitrogen atom of the alkyl group included in the amine com› pounds. The phenoxy group may have a substituent, such as  an alkyl group, an alkoxy group, a halogen atom, a cyano  group, a nitro group, a carboxyl group, a carboxylic ester  group, a sulfonic ester group, an aryl group, an aralkyl group,  an acyloxy group, and an aryloxy group.  This compound having at least one oxyalkylene chain  between the phenoxy group and the nitrogen atom are more  preferred. The number of oxyalkylene chains in one molecule  is preferably in the range of3 to 9, and more preferably 4 to 6.  Among the oxyalkylene chains, -CH$_{2}$CH$_{2}$0- is particu› larly preferable.  Specific  examples  thereof  include  2-[2-{2-(2,2- dimethoxy-phenoxyethoxy )ethy I }-bis-(2-methoxyethy I)]› amine, compounds (Cl-1) to (C3-3) exemplified in the para› graph 0066 ofUS2007/0224539Al, and the like.  The amine compound having a phenoxy group can be  obtained by, for example, first heating a primary or secondary  amine having a phenoxy group and a haloalkyl ether so as to  effect a reaction there between, subsequently adding an aque› ous solution of a strong base such as sodium hydroxide,  potassium hydroxide, and tetraalkylammonium, and thereaf› ter carrying out an extraction with an organic solvent such as  ethyl acetate and chloroform. Alternatively, the amine com› pound having a phenoxy group can be obtained by first heat› ing a primary or secondary amine and a haloalkyl ether hav› ing a phenoxy group at its end so as to effect a reaction  there between, subsequently adding an aqueous solution of a  strong base such as sodium hydroxide, potassium hydroxide,  and a tetraalkylammonium, and thereafter carrying out an  extraction with an organic solvent such as ethyl acetate and  chloroform.  ( 4) Ammonium Salt  As the basic compound, an ammonium salt may also be  suitably used. Examples of the anion of the ammonium salt  include halide, sulfonate, borate, and phosphate. Among  these, halide and sulfonate are particularly preferred.  The halide is particularly preferably chloride, bromide or  iodide.  The sulfonate is particularly preferably organic sulfonate  having 1 to 20 carbon atoms. Examples of the organic sul› fonate include an alkyl sulfonate and an aryl sulfonate each  having 1 to 20 carbon atoms.  The alkyl group contained in the alkyl sulfonate may have  a substituent. Examples of the substituent include a fluorine  atom, a chlorine atom, a bromine atom, an alkoxy group, an  acyl group, and an aryl group. Specific examples of the alkyl  sulfonate include methane sulfonate, ethane sulfonate, butane  sulfonate, hexane sulfonate, octane sulfonate, benzyl sul› fonate, trifluoromethane sulfonate, pentafluoroethane sul› fonate and nonafluorobutane sulfonate.  Examples of the aryl group contained in aryl sulfonate  include a phenyl group, a naphthyl group and an anthryl  group. These aryl groups may have a substituent. Preferred  examples of the substituent include a linear or branched alkyl  group having 1 to 6 carbon atoms and a cycloalkyl group  having 3 to 6 carbon atoms. Specific preferred examples  thereof include a methyl group, an ethyl group, an n-propyl  group, an isopropyl group, ann-butyl group, an i-butyl group,  at-butyl group, an n-hexyl group, and a cyclohexyl group.  Examples of the other substituent include an alkoxy group  having 1 to 6 carbon atoms, a halogen atom, a cyano group, a  nitro group, an acyl group and an acyloxy group.  The ammonium salt may be hydroxide or carboxylate. In  this case, the ammonium salt is particularly preferably tet› raalkylammonium hydroxide having 1 to 8 carbon atoms,  such as tetramethylammonium hydroxide, tetraethylammo› nium hydroxide and tetra-(n-butyl)anm10nium hydroxide.  Preferred examples of the basic compound include guani› dine, aminopyridine, aminoalkylpyridine, aminopyrrolidine,  indazole, imidazole, pyrazole, pyrazine, pyrimidine, purine,  imidazoline, pyrazoline, piperazine, aminomorpholine, and  aminoalkylmorpholine. They may further have a substituent.  Preferred examples of the substituent include an amino  group, an aminoalkyl group, an alkylamino group, an ami› noaryl group, an arylamino group, an alkyl group, an alkoxy  group, an acyl group, an acyloxy group, an aryl group, an  aryloxy group, a nitro group, a hydroxyl group, and a cyano  group.  Particularly preferred examples of the basic compound  include guanidine, 1,1-dimethyl guanidine, 1,1,3,3-tetram› ethyl guanidine, imidazole, 2-methylimidazole, 4-meth› ylimidazole, N-methylimidazole, 2-phenylimidazole, 4,5- diphenylimidazole,  2,4,5-triphenylimidazole,  2-aminopyridine, 3-aminopyridine, 4-aminopyridine, 2-dim› ethy laminopyridine,  4-dimethy laminopyridine,  2-diethy› laminopyridine, 2-(aminomethyl)pyridine, 2-amino-3-meth› ylpyridine,  2-amino-4-methylpyridine,  2-amino-5- methylpyridine,  2-amino-6-methylpyridine,  3-aminoethy !pyridine, 4-aminoethy !pyridine, 3-aminopyrro› lidine, piperazine, N-(2-aminoethyl)piperazine, N-(2-amino› ethy I )piperidine,  4-amino-2,2, 6, 6-tetramethy lpiperidine,  4-piperidinopiperidine, 2-iminopiperidine, 1-(2-aminoethyl)  pyrrolidine, pyrazole, 3-amino-5-methylpyrazole, 5-amino- 3-methyl-1-p-tolylpyrazole, pyrazine, 2-(aminomethyl)-5- methylpyrazine, pyrimidine, 2,4-diaminopyrimidine, 4,6- rO~O~OH  HO~N~o~o~OH  ("o~ O ~oH  ~N~o~ O HO~OH  HO~N~OH  -continued 