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3-Morpholino-1-(4-(2-oxopiperidin-1-yl)phenyl)-5,6-dihydropyridin-2(1H)-one

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3-Morpholino-1-(4-(2-oxopiperidin-1-yl)phenyl)-5,6-dihydropyridin-2(1H)-one Basic information

Product Name:
3-Morpholino-1-(4-(2-oxopiperidin-1-yl)phenyl)-5,6-dihydropyridin-2(1H)-one
Synonyms:
  • 5-morpholin-4-yl-1-[4-(2-oxopiperidin-1-yl)phenyl]-2,3-dihydropyridin-6-one
  • 3-Morpholino-1-[4-(2-oxo-1-piperidyl)phenyl]-5,6-dihydropyridin-2(1H)-one
  • 3-Morpholino-1-(4-(2-oxopiperidin-1-yl)
  • HSK00001094
  • Apixaban Impurity H
  • Apixaban Intermediates
  • Apixaban Impurity P
  • 3-Morpholin-4-yl-1-[4-(2-oxopiperidin-1-yl)phenyl]-5,6-dihydro-1H-pyridin-2-one
CAS:
545445-44-1
MF:
C20H25N3O3
MW:
355.43
EINECS:
1308068-626-2
Mol File:
545445-44-1.mol
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3-Morpholino-1-(4-(2-oxopiperidin-1-yl)phenyl)-5,6-dihydropyridin-2(1H)-one Chemical Properties

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
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3-Morpholino-1-(4-(2-oxopiperidin-1-yl)phenyl)-5,6-dihydropyridin-2(1H)-one Usage And Synthesis

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).

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