Asymmetric synthesis, crystal structure, and antidepressant activity of 2-aryl-3-alkyl-5-methyl-2-morpholinol hydrochlorides
Bibliographic record
Abstract
2-Aryl-3-alkyl-5-methyl-2-morpholinols were synthesized from the reactions of chiral 2-aminopropan-1-ol with 2-bromo-1-phenylpropan-1-one, 2-bromo-1-(3-chlorophenyl)propan-1-one, 1-(4-(benzyloxy)phenyl)-2-bromopropan-1-one, 2-bromo-1-(6-methoxy- naphthalen-2-yl)propan-1-one, and 1-(4-(benzyloxy)phenyl)pentan-1-one in N-methyl-2-pyrrolidone (NMP), respectively. The 2-aryl-3-alkyl-5-methyl-2-morpholinols were reacted with hydrogen chloride to give the hydrochloride salts with yields of 56%–77%. The structures of the products were proven by means of their 1H NMR, IR, and MS spectroscopic data. The stereochemical properties of representative products were established unambiguously by the X-ray single crystal analysis. The antidepressant activities of the title compounds were assayed by the mouse forced swimming test (FST). The FST results confirm the antidepressant properties of our products.Key words: morpholinol hydrochloride, hemiacetal, chiral synthesis, X-ray diffraction, absolute configuration, antidepressant activity.
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.001 | 0.000 |
Machine scores (provisional)
The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.
Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from itClassification
machine, unvalidatedMachine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.
How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".