Patent GB-307304-A (GB)
Title: Process for the manufacture of amino alcohols
Filed: 1929-03-04
Abstract: 307,304. I. G. Farbenindustrie Akt.- Ges. March 2, 1928, [Convention date]. Samples furnished. Amino alcohols of the formula- (in which R1 and R2 represent alkyl groups or hydrogen, X indicates an alkylaryl, alkylaminoaryl or alkyloxyaryl residue, R3 signifies hydrogen or an organic residue, and R4 represents an organic residue) are prepared by treating a compound of the formulawith a Grignard reagent of the formula Y.Mg.R4 (in which Y indicates a halogen). A solvent, such as ether or pyridine, may be employed. The products are yellowish viscous oils forming watersoluble crystalline salts with acids; they are of pharmaceutical value. Examples are given of the interaction of (1) diethylaminoacetone with the magnesium compounds of brombenzene, 4- bromanisol and #-bromethylbenzene, (2) 3-diethylamina-2-botanone with the magnesium compound of bromanisol, (3) 3-tetrahydroquinonyl-2- propanone with the magnesium compound of 4- brornphenetol, (4) 3:4-diethoxy-1-#-piperidinoacetopbenone with magnesium methyl iodide, 4- N - diethlyaminocthylmethylaminobenzaldehyde with the magnesium compound of 4-bromanisol, (2) 4 diethylaminoethylaminoacetophenone with magnesium bromphenetol, (3) the diethylaminoethylether of 2-hydroxybenzaldehyde and its 3. allyl derivative with magnesium ethyl bromide. The formulµ of the products are given. Grignard reagents of the formula, Y.Mg.R4, in which Y represents halogen and R. an organic residue, are obtained by treating a compound R4Y with magnesium in ethereal solution. The magnesium compounds of 4-bromanisol, 4-bromphenetol, and ethyl bromide are described. 4 - N-Diethylaminoethylaminobenzalde hyde results when N-methyl-p-aminobenzaldehyde is treated with diethylaminoethyl chloride.. 4-Diethylaminoethylaminoacetophenone is prepared by heating 4-aminoacetophenone and diethylaminoethyl chloride in benzene solution. 2-Hydroxybenzaldehyde diethylaminoethylether and its 3-allyl. derivative are obtained by condensing diethylaminoethyl chloride with 2-hydroxybenzaldehyde or its 3-allyl derivative in an alkaline medium. The Specification as open to inspection under Sect. 91 (3) (a) also includes the following subjectmatter :- Aminoalcohols.-The preparation is described of aminoalcohols of the above formula in which R1 and R2 are joint members of a nitrogen-containing heterocyclic ring, X indicates an aliphatic residue such as - CH2 - , - - C2H. -, - C,H - CH3, and in which R3 and R4, are mentioned as specifically including alkyl, aryl, aralkyl, hydroaromatic and heterocyclic residues. The Specification also contains examples of the interaction of (1) diethylaminoacetone with the magnesium compounds of brombenzene, 4-bromanisol and #-bromethylbenzene, (2) 3-diethylamino-2-butanone with the. magnesium compound of bromanisol. (3) 3-tetrahydroquinonyl-2-propanone, with the magnesium compound of bromanisol, (4) 3:-4-dietboxy-1-#-piperidino-acetophenone with magnesium methyl iodide. (5) 0)-di. ethvlaminoacetophenone with magnesium cyctohexyl bromide, (6) w-methylaminoacetophenone with magnesium methyl iodide (7) aminoacetone with phenylmagnesium bromide. The formulae of the products are given. Grignard reagents. - The preparation is described of Grignard reagents of the above formula in which R4 is stated specifically to represent alkyl, aryl, aralkyl, hydroaromatic and heterocyclic residues. The preparation of the magnesium compounds of brombenzene, )3-bromethylbenzene, methyl iodide and cyclohexyl bromide is given. 3-Tetrahydroquinonyl-2-propanone is prepared by heating tetrahydroquinoline with chloracetone. 3: 4-Dicthoxy-1-#-piperidino-acetophenone is obtained by alkylating the reaction product of piperidine and chloracetopyrocatechoi with toluene sulphonic ester. This subject-matter does not appear in the Specification as accepted.