58039-64-8

Usage

Uses

Used in Pharmaceutical Industry:
2-[2-phenylethyl]-morpholine is used as a key intermediate in the synthesis of various pharmaceutical compounds for its ability to form 2,4-disubstituted morpholines. These synthesized compounds are particularly effective in binding at human D4 dopamine receptors, which play a crucial role in the treatment of various central nervous system disorders, such as schizophrenia and other psychotic conditions.
The specific application of 2-[2-phenylethyl]-morpholine in the pharmaceutical industry lies in its utility as a building block for designing and developing novel drugs targeting the D4 receptor. By modulating the interactions at these receptors, the synthesized 2,4-disubstituted morpholines can potentially alleviate symptoms associated with the aforementioned disorders and contribute to the advancement of psychiatric therapeutics.

Upstream product

• 1126-76-7 1,2-Epoxy-4-phenylbutane 
• 926-39-6 sulfuric acid mono-(2-amino-ethyl ester) 
• 18328-11-5 3-benzyl propionaldehyde 
• 141916-53-2 2-chloro-4-phenylbutan-1-ol 
• 58040-19-0 4-benzyl-2-phenethylmorpholine 
• 1378834-52-6 2-chloro-4-phenylbutyraldehyde 
• 58040-18-9 4-cyano-2-(β-phenylethyl)morpholine 

Downstream Products

• 167273-43-0 MCO-III-157-Rac 

Relevant academic research and scientific papers

A Concise Stereoselective Synthesis of (R)-2-Benzylmorpholine and ML398 from (R)-(?)-2-Phenylglycinol

We describe here an efficient stereoselective method for the preparation of (R)-2-benzylmorpholine and ML398. The present method features a high diastereocontrol using an endocyclic oxidation of phenylglycinol-derived morpholine and a stereoselective alky

Discovery and characterization of ML398, a potent and selective antagonist of the D4 receptor with in vivo activity

Herein, we report the structure-activity relationship of a chiral morpholine-based scaffold, which led to the identification of a potent and selective dopamine 4 (D4) receptor antagonist. The 4-chlorobenzyl moiety was identified, and the compound was designated an MLPCN probe molecule, ML398. ML398 is potent against the D4 receptor with IC50 = 130 nM and Ki = 36 nM and shows no activity against the other dopamine receptors tested (>20 μM against D1, D2S, D2L, D3, and D5). Further in vivo studies showed that ML398 reversed cocaine-induced hyperlocomotion at 10 mg/kg.

A general, enantioselective synthesis of protected morpholines and piperazines

A short, high yielding protocol has been developed for the enantioselective and general synthesis of C2-functionalized, benzyl protected morpholines and orthogonally N,N′-protected piperazines from a common intermediate.

Binding of 2,4-substituted morpholines at human D4 dopamine receptors

The synthesis of a series of 2,4-disubstituted morpholines is described and their affinities at human dopamine receptors reported. The orally bioavailable 7-azaindole compound 11 has nanomolar affinity at the hD4 receptor with > 1000-fold selectivity over the hD2 receptor.

MORPHOLINE DERIVATIVES AS DOPAMINE RECEPTOR SUBTYPE LIGANDS

A class of substituted morpholine derivatives of formula STR1 wherein Y represents an optionally substituted bicyclic heteroaromatic ring system containing one or two nitrogen atoms, the ring system comprising a six-membered aromatic or heteroaromatic ring fused to a five-or six-membered heteroaromatic ring; and Z represents an optionally substituted arylalkyl, aryloxymethyl or arylalkoxymethyl group, are ligands for dopamine receptor subtypes within the body and are therefore useful in the treatment and/or prevention of disorders of the dopamine system, in particular schizophrenia.

Phenylvinyl morpholine compounds

Morpholine derivatives, typically those of the formula: STR1 wherein A is an ethylene or vinylene radical and X is a phenyl radical optionally substituted by one or two substituents selected from halogen atoms, alkyl and alkoxy radicals of 1 to 6 carbon a