3-Morpholino-1-(4-(2-oxopiperidin-1-yl)phenyl)-5,6-dihydropyridin-2(1H)-one
- CAS No.
- 545445-44-1
- Chemical Name:
- 3-Morpholino-1-(4-(2-oxopiperidin-1-yl)phenyl)-5,6-dihydropyridin-2(1H)-one
- Synonyms
- 5,6-Dihydro-3-(4-morpholinyl)-1-[4-(2-oxo-1-piperidinyl)phenyl]-2(1H)-pyridinone;in-4-yL;Apixaban-1;HSK00001094;Apixaban Impurity H;Apixaban Impurity P;RSYY(Apremilast)-36;Apixaban Intermediates;Apixaba inretMediate B;Apixaban Intermediate 2
- CBNumber:
- CB62534569
- Molecular Formula:
- C20H25N3O3
- Molecular Weight:
- 355.43
- MOL File:
- 545445-44-1.mol
- MSDS File:
- SDS
- Modify Date:
- 2023/9/7 16:59:03
Melting point | >199°C (dec.) |
---|---|
Boiling point | 625.0±55.0 °C(Predicted) |
Density | 1.267 |
storage temp. | 2-8°C |
solubility | Chloroform (Slightly), Methanol (Slightly) |
form | Solid |
pka | 3.25±0.20(Predicted) |
color | Pale Beige |
InChI | InChI=1S/C20H25N3O3/c24-19-5-1-2-10-22(19)16-6-8-17(9-7-16)23-11-3-4-18(20(23)25)21-12-14-26-15-13-21/h4,6-9H,1-3,5,10-15H2 |
InChIKey | SCVWQFDPLBFZAP-UHFFFAOYSA-N |
SMILES | C1(=O)N(C2=CC=C(N3CCCCC3=O)C=C2)CCC=C1N1CCOCC1 |
3-Morpholino-1-(4-(2-oxopiperidin-1-yl)phenyl)-5,6-dihydropyridin-2(1H)-one Chemical Properties,Uses,Production
Uses
3-Morpholino-1-(4-(2-oxopiperidin-1-yl)phenyl)-5,6-dihydropy can be used as an organic synthesis intermediate, mainly used in laboratory research and development and chemical production processes.
Synthesis
2 g compound C (compound Ib) and 50 ml acetonitrile were added into a three-necked flask to obtain a turbid solution. The turbid solution was stirred and cooled to 0?? C. in an ice bath. 1.75 g (6 eq) sodium hydroxide was added and stirred in the ice bath for 10 min. Then 1.9 ml of 5-chloro-valeryl chloride (2 eq) (diluted with 2 ml acetonitrile) was dropwise added while controlling the temperature to 0-5?? C. After completing the addition, the ice bath was removed and the temperature was naturally raised to 30?? C. The reaction was performed for 5 hours. After observing the absence of the starting material and the intermediate state of the reaction, the reaction solution was cooled to 0?? C. in an ice bath, and adjusted to a neutral pH with 6 N of hydrochloric acid. The reaction solution was concentrated to dryness, pulpifying for 1 hour after adding 8 ml saturated sodium bicarbonate solution, and filtered to obtain 2.29 g yellow solid. Yield: 87.5%. Purity: 95.3% (HPLC). EI-MS (m/z): 355.2. HNMR (400 MHz, DMSO, ppm) |?7.32 (d, J=8.8 Hz, 2H), 7.26 (d, J=8.8 Hz, 2H), 5.71 (t, J=4.8 Hz, 1H), 3.72-3.69 (m, 2H), 3.65-3.63 (m, 4H), 3.60-3.57 (m, 2H), 2.79-2.77 (m, 4H), 2.44-2.41 (m, 2H), 2.40-2.39 (m, 2H), 1.88-1.82 (m, 4H).
3-Morpholino-1-(4-(2-oxopiperidin-1-yl)phenyl)-5,6-dihydropyridin-2(1H)-one Preparation Products And Raw materials
Raw materials
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