72662-80-7

Upstream product

• 26475-66-1 4-benzylthiomorpholine 1,1-dioxide 
• 123-90-0 Thiomorpholin 
• 100-51-6 benzyl alcohol 
• 100-46-9 benzylamine 
• 1233656-18-2 C₁₆H₁₉O₄P 

Downstream Products

• 26475-66-1 4-benzylthiomorpholine 1,1-dioxide 

Relevant academic research and scientific papers

Direct: N -alkylation of sulfur-containing amines

An efficient ruthenium-catalyzed method has been developed for the direct N-alkylation of sulfur-containing amines with alcohols, for the first time, by a step-economical and environmentally friendly hydrogen borrowing strategy. The present methodology features base-free conditions and broad substrate scope, with water being the only by-product. Moreover, this protocol has been applied to the synthesis of the pharmaceutical drug Quetiapine.

Application of bis(triphenylphosphine)carbonyl ruthenium dichloride monohydrate

The invention provides bis(triphenylphosphine)carbonyl ruthenium dichloride monohydrate. A preparation method comprises the following steps: adding triphenylphosphine into an organic solvent A, and conducting heating to 50-100 DEG C to dissolve the triphenylphosphine so as to obtain a solution A; adding ruthenium trichloride into an organic solvent B, and conducting dissolving to obtain a solution B; then sequentially and rapidly adding the solution B and an aqueous formaldehyde solution with a mass fraction of 37% into the solution A, and conducting a reaction for 0.5-2 h at a temperature of 80-130 DEG C; and carrying out post-treatment on the obtained reaction solution A to obtain the bis(triphenylphosphine)carbonyl ruthenium dichloride monohydrate. Compared with a synthesis method proposed by Colt and the like, the method disclosed by the invention has the advantages that the use of strong acid can be well avoided, injury to operators in an experiment process is reduced, reaction time is greatly shortened, treatment after the experiment is simple, and experiment efficiency is improved.

Preparation method of bis(triphenylphosphine) carbonyl ruthenium dichloride monohydrate

The invention provides bis(triphenylphosphine) carbonyl ruthenium dichloride monohydrate, which is prepared by the following steps of adding triphenylphosphine into an organic solvent A, and heating to 50-100 DEG C to dissolve the triphenylphosphine to obtain a solution A, adding ruthenium trichloride into an organic solvent B, and dissolving to obtain a solution B, then sequentially and rapidly adding the solution B and a formaldehyde aqueous solution with the mass fraction of 37% into the solution A, and conducting a reaction for 0.5-2 h at the temperature of 80-130 DEG C, and carrying out post-treatment on the obtained reaction liquid A to obtain the bis(triphenylphosphine) carbonyl ruthenium dichloride monohydrate. Compared with a synthesis method of Colt et al., the method disclosed by the invention has the advantages that the use of strong acid can be well avoided, the injury to operators in the experiment process is reduced, the reaction time is greatly shortened, the treatment after the experiment is simple, and the experiment efficiency is improved.

Mitsunobu Reaction Using Basic Amines as Pronucleophiles

A novel protocol for extending the scope of the Mitsunobu reaction to include amine nucleophiles to form C-N bonds through the utilization of N-heterocyclic phosphine-butane (NHP-butane) has been developed. Both aliphatic alcohols and benzyl alcohols are suitable substrates for C-N bond construction. Various acidic nucleophiles such as benzoic acids, phenols, thiophenol, and secondary sulfonamide also provide the desired products of esters, ethers, thioether, and tertiary sulfonamide with 43-93% yields. Importantly, C-N bond-containing pharmaceuticals, Piribedil and Cinnarizine, have been synthesized in one step from the commercial amines under this Mitsunobu reaction system.

Oxidation-Reduction Condensation of Diazaphosphites for Carbon-Heteroatom Bond Formation Based on Mitsunobu Mechanism

An efficient oxidation-reduction condensation reaction of diazaphosphites with various nonacidic pronucleophiles in the presence of DIAD as a weak oxidant has been developed for carbon-heteroatom bond formation. This mild process affords structurally diverse tertiary amines, secondary amines, esters, ethers, and thioethers in moderate to excellent yields. The selective synthesis of secondary amines from primary amines has been achieved. Importantly, a practical application to the synthesis of antiparkinsonian agent piribedil has been demonstrated.

ROMP-derived oligomeric phosphates for application in facile benzylation

The development of new ROMP-based oligomeric benzyl phosphates (OBP n) is reported for use as soluble, stable benzylating reagents. These oligomeric reagents are readily synthesized from commercially available materials and conveniently polymerized and purified in a one-pot process, affording bench-stable, pure white, free-flowing solids on multigram scale. Utilization in benzylation reactions with a variety of nucleophiles is reported.

Synthesis of Piperazines and Thiomorpholines by Ozonolysis of Cyclic Olefins and Reductive N-Alkylation

Ozonized 1-trifluoroacetyl-3-pyrroline (2a) and 3-sulfolene (6) were reduced with sodium cyanoborohydride (1) to afford the dialdehyde, which reacted in situ with the primary amines 3ad in the presence of 1 to give the piperazines 4ad (2160 percent) and the dioxothiomorpholines 7ad (2676 percent).Reduction of 7a and 7c with diisobutylaluminum hydride yielded the thiomorpholines 8a and 8c, respectively.On the other hand, the 9-membered azacrown ethers 10 and 11 were obtained when N,N'-dibenzylethylenediamine (9) was employed.The dioxothiomorpholine derivatives 13 of amino acids were also prepared by the same treatment.