Ethyl Acetate → 1-[3-(4-Butyl-piperidin-1-yl)propyl]-7-methyl-1H-quinolin-2-one

HRID 969430Notes

Reaction equation

HRID 969430 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH3:15])[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].CCOC(C)=O>CC#N.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](=[CH:10][CH:11]=[C:12]([CH3:15])[CH:13]=3)[CH:8]=[CH:7][C:6]2=[O:16])[CH2:29][CH2:28]1)[CH2:24][CH2:25][CH3:26]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 132838674-ButylpiperidineHCID 179561161-(3-Chloropropyl)-7-methyl-1H-quinolin-2-one

Product 1

HCID 179560921-[3-(4-Butyl-piperidin-1-yl)propyl]-7-methyl-1H-quinolin-2-oneYield 8.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A 4 mL vial was charged with 1-(3-chloro-propyl)-7-methyl-1H-quinolin-2-one 107LH40 (0.130 g, 0.56 mmol), KI (0.170 g, 1.0 mmol), K2CO3 (0.140 g, 1.0 mmol) and 4-butylpiperidine (100 μl, 0.60 mmol) in CH3CN (2 mL). The mixture was shaken at 50° C. for 72 h and then poured onto The compound EtOAc (25 mL) and 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 (0.017 g, 6%). 1H NMR (CD3OD) δ 7.84 (d, J=9.4 Hz), 7.56 (d, J=8.0 Hz, 1H), 7.43 (brs, 1H), 7.14 (brd, J=8 Hz, 1H), 6.58 (d, J=9.4 Hz), 4.36 (d, J=7.2 Hz, 2 H), 3.02-2.95 (m, 2H), 2.57-2.48 (m, 2H), 2.51 (s, 3H), 2.09-1.91 (m, 4H), 1.75-1.65 (m, 2H9, 1.36-1.16 (m, 9H), 0.89 (t, J=6.8 Hz, 3H); 13C NMR (CD3OD) δ 163.3, 142.2, 140.3, 139.1, 129.1, 124.1, 119.3, 119.0, 114.7, 55.6, 53.8, 40.4, 36.1, 35.5, 31.8, 28.9, 24.6, 22.7, 21.1, 13.2; HPLC-MS (ammonium acetate) [M+H]+=341.3.

Workup

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

Sources & evidence

ORD record
ord-67eba78db6e643009b95dd463f2f0363
Source dataset
uspto-grants-2007_12
Patent number
US07307075B2

Reaction notes

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