Aminomethyl tetrahydropyranyl derivatives

摘要

The invention comprises 2-aminomethyltetrahydropyran-6-yl derivatives of the general formula where R1 and R2 represent hydrogen, hydrocarbon radicals, acyl radicals or radicals of the formula -CH2OR, wherein R represents hydrogen or C1- 4 alkyl, or R1 and R2 taken togethe form an alkylene or substituted alkylene group forming a 5- or 6-membered ring with the nitrogen atom, R1 and R4 are hydrogen, halogen or C1- 4 alkyl, R5 represents the residue of an active hydrogen-containing compound R5(H)n containing at least n active hydrogen atoms and n represents an integer. They may be obtained by reacting a 3,4-dihydro-3-4-pyran compound of the formula with an active hydrogen-containing compound in the presence of an acidic catalyst and optionally in the presence of an inert solvent. The residue R5 may be derived from a hydroxy group-containing polyether, e.g. a polyether of the general formula where A and B are hydrogen or methyl, x is an integer, preferably of at least 2, y is an integer, preferably 1 to 8, and R6 represents alkyl or aryl, or hydrogen when y=1, and the number of polyalkylene oxy radicals is preferably such that the molecular weight of the hydroxyl compound is from 200 to 6000. The examples, of which there are many, include compounds in which the residue R5 is derived from (i) an hydroxyl ended polymer of an alkylene oxide, (ii) the polymerization product of an alkylene oxide with a monohydric alcohol or phenol, a polyol or a mono- or di-carboxylic acid, (iii) a phenol-formaldehyde reaction product, (iv) an oxypropylated resole, and (v) a hydroxyl-ended polyethylene adipate.ALSO:The invention comprises 2-aminomethyl-tetrahydropyran-6-yl derivatives of the general formula where R1 and R2 represent hydrogen, hydrocarbon radicals, acyl radicals or radicals of the formula -CH2OR, wherein R represents hydrogen or C1- 4 alkyl, or R1 and R2 taken togethe form an alkylene or substituted alkylene group forming a 5- or 6-membered ring with the nitrogen atom, R3 and R4 are hydrogen, halogen or C1- 4 alkyl, R5 represents the residue of an active hydrogen-containing compound R5(H)n containing at least n active hydrogen atoms and n represents an integer. They may be obtained by reacting a 3,4-dihydro-2H-pyran compound of the general formula with an active hydrogen-containing compound in the presence of an acidic catalyst and optionally in the presence of an inert solvent. The compounds exemplified include 2-N,N-dimethylaminomethyl - 6 - ethoxytetrahydropyran, 2 - aminomethyl - 6 - ethoxytetrahydropyran, 2 - N,N - dimethylaminomethyl - 3,4 - dihydro - 2H - pyran, 2 - N,N - dimethylaminomethyl - 6 - (carbethoxymethylthio) tetrahydropyran, 2 - N,N - dimethylaminomethyl-6 - (21,H1 - dichlorophenoxy) tetrahydropyran and compounds of the formulae