Potassium Carbonate → 1-[3-(4-Butylpiperidin-1-yl)propyl]-5-methyl-1H-quinolin-2-one

HRID 2103295Notes

Reaction equation

HRID 2103295 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[C:10]([CH3:15])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]1=[O:16].C([O-])([O-])=O.[K+].[K+].[CH2:23]([CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[CH2:24][CH2:25][CH3:26]>CC#N.CCOC(C)=O>[CH2:23]([CH:27]1[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][CH2:4][N:5]2[C:14]3[C:9](=[C:10]([CH3:15])[CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7][C:6]2=[O:16])[CH2:29][CH2:28]1)[CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 132838674-ButylpiperidineHCID 179560681-(3-chloropropyl)-5-methyl-1H-quinolin-2-one

Product 1

HCID 179561711-[3-(4-Butylpiperidin-1-yl)propyl]-5-methyl-1H-quinolin-2-oneYield 74.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A 4 mL vial was charged with 1-(3-chloropropyl)-5-metyl-1H-quinolin-2-one (0.053 g, 0.23 mmol), KI (0.083 g, 0.5 mmol), K2CO3 (0.069 g, 0.50 mmol) and 4-butylpiperidine (50 μl, 0.30 mmol) in CH3CN (2 mL). The mixture was shaken at 50° C. for 72 h and then diluted with EtOAc (25 mL) and washed with water (15 mL). The water phase was extracted (2×25 mL) and the combined organic phases were dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by flash CC (SiO2; EtOAc/MeOH 1:4) to give the title compound (0.058 g, 74%). 1H NMR (CD3OD) δ 8.13 (d, J=9.8 Hz, 1H), 7.56-7.46 (m, 2H), 7.15 (brd, 6.8 Hz, 2H), 6.67 (d, J=9.8 Hz, 1H), 4.38 (t, J=7.2 Hz, 2H), 3.10-3.03 (m, 2H), 2.68-2.61 (m, 2H), 2.57 (s, 3H), 2.25-2.15 (m, 2H), 2.04-1.95 (m, 2H), 1.78-1.69 (m, 2H), 1.36-1.16 (m, 9H), 0.89 (t, J=7.0 Hz, 3H); 13C NMR (CD3OD) δ 162.3, 138.7, 136.6, 136.2, 130.4, 123.6, 119.4, 118.9, 112.4, 54.7, 52.9, 39.9, 35.3, 34.5, 30.7, 28.2, 23.7, 22.1, 17.3, 12.6; HPLC-MS (ammonium acetate) [M+H]+=341.3.

Workup

  1. washwashed with water (15 mL)
  2. extractionThe water phase was extracted (2×25 mL)
  3. dry with materialthe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash CC (SiO2; EtOAc/MeOH 1:4)

Sources & evidence

ORD record
ord-42dacdcc35b140688692b71d1e1bb694
Source dataset
uspto-grants-2009_08
Patent number
US07576100B2

Reaction notes

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