1156-05-4 Usage
Originator
Ciba 10870, Ciba Pharmaceutical
Manufacturing Process
350 parts by weight of the potassium salt of 2-phenyl-2-(βdiethylaminoethyl)-pentane-1,5-diacid mononitrile are dissolved with heating in 700 parts by volume of glacial acetic acid, 850 parts by volume of acetic anhydride are added, and then 250 parts by volume of concentrated sulfuric acid introduced portionwise. The temperature of the reaction mixture in this operation rises to 120-130°C. When the reaction subsides, the whole is finally maintained for a further 15 min on the boiling water bath. The solvent is removed on the water bath under reduced pressure, the residue poured onto ice and caustic soda solution, and the whole extracted with chloroform. The chloroform solution washed with water, dried over potassium carbonate and the solvent evaporated. The crystalline residue, consisting of 3-phenyl-3-(βdiethylaminoethyl)-2,6-dioxopiperidine. After recrystallization from a mixture of ethyl acetate and ligroin, melts at 118-120°C.The hydrochloride (produced by dissolving the base in ethyl acetate and adding an equivalent quantity of hydrochloric acid gas dissolved in ethylacetate) melts, after recrystallization from a mixture of methyl alcohol and ethyl acetate, at 168-172°C.
Therapeutic Function
Anticholinergic, Antiparkinsonian
Check Digit Verification of cas no
The CAS Registry Mumber 1156-05-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,5 and 6 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 1156-05:
(6*1)+(5*1)+(4*5)+(3*6)+(2*0)+(1*5)=54
54 % 10 = 4
So 1156-05-4 is a valid CAS Registry Number.
InChI:InChI=1S/C17H24N2O2/c1-3-19(4-2)13-12-17(14-8-6-5-7-9-14)11-10-15(20)18-16(17)21/h5-9H,3-4,10-13H2,1-2H3,(H,18,20,21)
1156-05-4Relevant articles and documents
On the Relocation of the Amino Functionality to the Ethyl Side Chain in Aminoglutethimide: Synthesis and Aromatase-inhibitory Activity of 3-(2′-N,N-Diethylamino)ethyl-3-phenylpiperidine-2,6-dione
Moniz, George A.,Hammond, Gerald B.
, p. 649 - 652 (2007/10/03)
Aminoglutethimide [3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione] has been used clinically in the treatment of metastatic breast carcinoma. Inhibition of tumor growth is due to interference with estrogen biosynthesis. However, its action is not specific and its metabolism gives rise to toxic and non-inhibitory metabolites. We sought to explore the impact of relocating the amino group in aminoglutethimide to the ethyl side chain. To that end, we now report the synthesis and aromatase-inhibitory activity of 3-(2′-N,N-diethylamino)ethyl-3-phenylpiperidine-2,6-dione 5. The introduction of the amino functionality on the ethyl group is accomplished via reductive amination of aldehyde 8, prepared in three steps from benzyl cyanide, The synthetic route presented can be used for the preparation of related derivatives of azninoglutethimide.
