1,3-Dimethylpiperidone-4

Abstract

A piperidone-4 with a suitable alkyl substituent in the 3-position could conceivably function as starting material for a synthesis of homomeroquinene (2);* no compound of this type has been reported in the literature (3). This paper describes the preparation of 1,3-dimethylpiperidone-4 (IV) by the steps outlined below; this type of synthesis has been employed extensively by McElvain and co-workers (4).

Optimization of the Manufacturing Technology for Promedone. Synthesis of 1,2,5-trimethylpiperidin-4-one

“…This was prepared as described in [3] as a colorless liquid. The yield was 75%, the melting temperature was 61-63°C/15 mm, n (6); 100 (2); 70 (4); 57 (3); 44 (100).…”

“…A large number of methods are known for the synthesis of piperidone-4 compounds, though the most widely used in industry is Dieckmann intramolecular condensation [3][4][5][6]. The main advantages of this method are the regiospecificity of the cyclization reaction and the absence of side compounds with physicochemical properties close to those of the target product, hindering its purification.…”

Nucleophilic Addition of Amino-groups to an Activated Carbon–Carbon Double Bond

“…Thus in the presence of methanol the reactions of lower amines and dialkylamines (and also benzylamine) give, after a fairly long time, high yields of the corresponding monoadducts even at a low temperature I23,i27,i28,i37,i42,i6o,i64 # With me thylamine, a small amount of the double addition product is also obtained 123 . Hexamethyleneimine, /3-tetrahydronaphthylamine, and cyclohexylamine react with methyl methacrylate on heating in the presence of added alcohol-the reaction takes place smoothly without the formation of side products 121 7 i^.…”

“…Non-catalytic reactions of methacrylates with a number of aliphatic and aliphaticaromatic amines have also been described i24,i4o,i65 # However, the addition of methyl methacrylate, on refluxing the mixture, to dibutylamine 123 , ethyl JV-methylaminopropionate 123 > 141 , and t-butylamine 166 could not be achieved. Aniline reacts with methyl methacrylate at 200°C to give a low yield of a mixture of three substances: the normal addition product, the anilide of 3-anilino-2-methylpropionic acid, and methacrylanilinide 120 .…”

Substituierte 2,8‐Diazaspiro[4,5]decan‐1, 3‐dione. Untersuchungen über synthetische Arzneimittel, 16. Mitteilung

“…C 7O,6 H 7,4 0 11,7 N 10,3y0 (272.35) Cnf. ,,70,8 ,,7,3 ,,11.7 ,,10, C,,H,,N,,HCl Ber. C 74,O H 6,5 N 8.6 C1 10,9% (324,74) Gef.…”