20245-73-2

Upstream product

• 110-91-8 morpholine 
• 96-09-3 styrene oxide 
• 22083-23-4 α-morpholine ethyl phenylacetate 

Downstream Products

• 96067-86-6 diphenyl-acetic acid 2-morpholin-4-yl-2-phenyl-ethyl ester 

Relevant academic research and scientific papers

Lithium trifluoromethanesulfonate-catalysed aminolysis of oxiranes

The aminolysis of oxiranes was found to be catalysed by lithium trifluoromethanesulfonate in acetonitrile solutions. This salt turned out to be an excellent substitute for the unsafe lithium perchlorate.

Synthesis and application of Cu(II) immobilized MCM-41 based solid Lewis acid catalyst for aminolysis reaction under solvent-free condition

In this paper, a Cu(II) immobilized periodic mesoporous organosilica (PMOs) was synthesized and used as a reusable solid Lewis acid catalyst for the aminolysis of epoxides under solvent-free conditions. An amide-based ligand, L-propylsilyl (1) having a specific binding pocket was prepared and fabricated on mesoporous MCM-41 to produce mesoporous organosilica L-propylsilyl@MCM-41 (2). Further, it has been utilized for anchoring Cu(II) ions under controlled reaction conditions to yield solid Lewis acid catalyst Cu(II)-L-propylsilyl@MCM-41 (3). The synthesized catalyst 3 exhibits significantly higher catalytic activity for aminolysis compared to hitherto known solid Lewis acid catalysts. An extensive range of β-amino alcohols with high regio and stereoselectivity were prepared by using catalyst 3. The catalyst was recovered easily and reused eight times without any loss in its catalytic activity. Furthermore, the synthesis of clinically significant propranolol (β-blocker) from α- naphthyl glycidyl ether was attained successfully using catalyst 3 in a very decent yield.

Greener aminolysis of epoxides on BiCl3/SiO2

The remarkable catalytic activity of BiCl3/SiO2 for the ring-opening of epoxides with aromatic and aliphatic amines under microwave and thermal heating was observed. This eco-friendly heterogeneous catalyst displayed high to excellent regioselectivity in the synthesis of β-amino alcohols under solvent-free conditions. High turnover frequency (TOF) values under microwave heating and excellent reusability of the catalyst may significantly contribute to applied chemistry.

Mild regiospecific alcoholysis and aminolysis of epoxides catalyzed by zirconium(IV) oxynitrate

A regiospecific method for the ring-opening reaction of epoxides by the primary, secondary, tertiary alcohols, and aryl, aliphatic amines has been developed using non-toxic metal nitrate salt as a catalyst. The best results were obtained using zirconium(IV) oxynitrate among the various screened metal nitrate salts. The reported protocol works efficiently for styrene epoxide and aliphatic as well.

Regioselective ring-opening of aziridines and epoxides with amines under catalyst- and solvent-free condition on solid phase

Ring opening of aziridines and epoxides with various amines afforded high regioselective products in high yields by solid phase reaction under catalyst- and solvent- free condition. The ring opening reaction proceeded rapidly by grinding.

Aminolysis of epoxides catalyzed by three-dimensional, mesoporous titanosilicates, Ti-SBA-12 and Ti-SBA-16

The application of three-dimensional, mesoporous titanosilicates (Ti-SBA-12 and Ti-SBA-16) as reusable, solid catalysts for the synthesis of a range of β-amino alcohols in high yields and selectivity through ring-opening of epoxides with amines at ambient

Mg(ClO4)2, an efficient catalyst for synthesis of β-amino alcohols by ring opening of epoxides with amines under solvent-free conditions

Commercially available magnesium perchlorate is reported as an extremely efficient catalyst for the ring-opening reaction of epoxide with various primary and secondary amines, especially diphenyl amine, under solvent-free conditions at room temperature.

Zinc tetrafluoroborate hydrate as a mild catalyst for epoxide ring opening with amines: Scope and limitations of metal tetrafluoroborates and applications in the synthesis of antihypertensive drugs (RS)/(R)/(S)-metoprolols

The scope and limitations of metal tetrafluoroborates have been studied for epoxide ring-opening reaction with amines, and Zn(BF4) 2?xH2O has been found to be a mild and efficient catalyst affording high yields under solvent-free conditions at rt with excellent chemo-, regio-, and stereoselectivities. The catalytic efficiency followed the order Zn(BF4)2?xH2O ? Cu(BF4)2?xH2O > Co(BF4) 2?6H2O ? Fe(BF4)2? 6H2O > LiBF4 for reactions with cyclohexene oxide and Zn(BF4)2?xH2O ? Co(BF4) 2?6H2O ? Fe(BF4)2? 6H2O > Cu(BF4)2?xH2O for stilbene oxide, but AgBF4 was ineffective. For reaction of styrene oxide with aniline, the metal tetrafluoroborates exhibited comparable regioselectivity (1:99-7:93) with preferential reaction at the benzylic carbon of the epoxide ring. A reversal of regioselectivity (91:1-69:31) in favor of the reaction at the terminal carbon of the epoxide ring was observed for reaction with morpholine. The regioselectivity was dependent on the electronic and steric factors of the epoxide and the pKa of the amine and independent of amine nucleophilicity. The role of the metal tetrafluoroborates is envisaged as "electrophile nucleophile dual activation" through cooperativity of coordination, charge-charge interaction, and hydrogen-bond formation that rationalizes the catalytic efficiency, substrate reactivity, and regioselectivity. The methodology was used for synthesis of cardiovascular drug metoprolol as racemic and enriched enantiomeric forms.

Highly efficient and versatile chemoselective addition of amines to epoxides in water catalyzed by erbium(III) triflate

Er(OTf)3 is proposed as a highly efficient and reusable catalyst for the opening of epoxides in water with aliphatic as well as aromatic amines leading to the synthesis of β-amino alcohols. The aqueous conditions employed in the present method will make it 'environmentally friendly' and potentially useful for industrial applications.

Microwave-enhanced bismuth triflate-catalyzed epoxide opening with aliphatic amines

In the presence of a catalytic amount of Bi(OTf)3·4H2O and under microwave irradiation, neat mixtures of epoxides and amines afforded smoothly the corresponding 2-amino alcohols. A wide variety of aliphatic amines were reacted with cycloalkene oxide, styrene oxide, and stilbene oxide. The reaction proceeded rapidly and afforded the 2-amino alcohols in high up to quantitative yields. All products could be obtained without aqueous work-up by simple filtration.