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ChemicalBook CAS DataBase List 1,2-Ethanedione, 1-phenyl-2-(1-piperidinyl)- Piperidine, 1-(oxophenylacetyl)- (9CI)
14377-63-0

1,2-Ethanedione, 1-phenyl-2-(1-piperidinyl)- Piperidine, 1-(oxophenylacetyl)- (9CI) synthesis

13synthesis methods
-

Yield:14377-63-0 86%

Reaction Conditions:

with selenium(IV) oxide;sulfuric acid in 1,4-dioxane at 80;Reagent/catalyst;

Steps:

B: Standard reaction procedure terminal alkyne
General procedure: B: Standard reaction procedure terminal alkyne: SeO2 (1.0 mmol) was added to a solutionof terminal alkyne (1.0 mmol) in dioxan (1 ml) followed by the addition of 10mol% of H2SO4 and amine (1.0 mmol). The reaction mixturewas then heated at 80oC for 10-12 h and the product formation wasmonitored by TLC. After completion, reaction mixture was partioned with waterethyl acetate, extracted with ethyl acetate (3 x 50ml). The combined organiclayers were washed with brine solution, concentrated on rotary evaporator andpurified by column chromatography using ethyl acetate and hexane to affordcorresponding pure products. Spectral data:N,N-diethylbenzamide (3a): 1H NMR (CDCl3,400 MHz): δH 7.26-7.40 (m,5H), 3.54 (s, 2H), 3.25 (s, 2H), 1.25(s, 3H), 1.10 (s, 3H); 13CNMR (CDCl3, 100 MHz): δc 171.32, 137.33, 129.10, 128.41, 126.28, 42.29, 39.23,14.23, 12.93. ESIMS: m/z 178.12 [M+H]+, Yield 90%.

References:

Meena, Samdarshi;Singh, Rohit;Vishwakarma, Ram A.;Aga, Mushtaq A.;Jain, Shreyans K. [Tetrahedron Letters,2016,vol. 57,# 33,p. 3715 - 3717] Location in patent:supporting information

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