Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hexane | HCID 8058 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 2-Aminomethyl-4-(4-fluorobenzyl)morpholine | HCID 10242735 | — |
| Reactant | HCID 90386549 | HCID 90386549 | — |
| Product | HCID 71495426 | HCID 71495426 | 53% |
Reaction Steps
The solution obtained in step 1 was cooled to 4-5° C. in an ice bath, followed by dropwise adding triethylamine (0.42 ml, 3.0 mmol) for 5 min. To the reaction solution was added with 4-(4-fluorobenzyl)morpholin-2-ylmethylamine (1.2 mmol), and stirred for 30 min at a room temperature and then for an additional 4 hrs under reflux. The reaction mixture was cooled to a room temperature, and washed with saturated aqueous sodium hydrogen carbonate solution and then with saturated saline. After water was removed with a desiccant, the resulting solution was concentrated in a reduced pressure. In order to obtain a desired fraction, the residue was subjected to silica column chromatography (mobile phase: 30 (v/v) % Hexane in EA) to afford the title compound (Total yield: 53.0%)1H NMR (CDCl3) δ 8.20 (d, 1H), 8.12 (d, 1H), 7.54 (d, 1H), 7.36-7.24 (m, 7H), 7.01 (t, 2H), 6.46-6.38 (m, 1H), 4.08-3.98 (m, 1H), 3.87 (d, 1H), 3.73-3.61 (m, 4H), 3.53 (s, 2H), 3.45 (s, 2H), 3.32-3.19 (m, 2H), 2.85-2.61 (m, 4H), 2.32-2.14 (m, 3H), 2.08-1.88 (m, 3H) ppm.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09227955B2 |
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| Source dataset | uspto-grants-2016_01 |
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| ORD ID | ord-513bb944bcea4781b66f081a0e710a33 |
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| Source note | uspto-grants-2016_01 |
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