Acetic Acid → HCID 66597051, compound

HRID 1811425Notes

Reaction equation

HRID 1811425 reaction equation
Cl[CH2:2][C:3]1[N:8]=[C:7]([CH2:9][N:10]2[C:19]3[C:14](=[C:15]([CH:20]4[O:24][CH2:23][CH2:22][O:21]4)[CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][C:11]2=[O:25])[CH:6]=[CH:5][CH:4]=1.[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.O.C(O)(=O)C>C(OCC)(=O)C>[O:21]1[CH2:22][CH2:23][O:24][CH:20]1[C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:14]=1[CH2:13][CH2:12][C:11](=[O:25])[N:10]2[CH2:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:2][N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[N:8]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 8082PiperidineHCID 66596821HCID 66596821, compound

Product 1

HCID 66597051HCID 66597051, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

1-(6-Chloromethylpyridin-2-ylmethyl)-5-(1,3-dioxolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (1.0 g, 2.8 mmol) was added to piperidine (2 ml), followed by stirring in an argon atmosphere at 100° C. for 2 hours. After cooling to room temperature, water and a small quantity of acetic acid were added to the reaction mixture, and extraction with ethyl acetate was performed twice. The organic layers were combined, washed twice with water and once with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The dry product was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1). The purified product was concentrated to dryness under reduced pressure to thereby obtain 0.73 g (yield: 64%) of 5-(1,3-dioxolan-2-yl)-1-(6-piperidinomethylpyridin-2-ylmethyl)-3,4-dihydro-1H-quinolin-2-one as a light yellow amorphous solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed twice with water and once with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe dry product was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1)
  6. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-96a94a0072ac4426b6631e9c963d8573
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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