Diisopropylethylamine → 4-(4-Methoxybenzoyl)[1,3'-bipiperidin]-2'-one

HRID 1752239Notes

Reaction equation

[O:1]=[C:2]1[CH:7](OS(C)(=O)=O)[CH2:6][CH2:5][CH2:4][NH:3]1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[O:22])=[CH:17][CH:16]=1.C(N(C(C)C)CC)(C)C>C(#N)C>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]([CH:23]2[CH2:28][CH2:27][N:26]([CH:7]3[CH2:6][CH2:5][CH2:4][NH:3][C:2]3=[O:1])[CH2:25][CH2:24]2)=[O:22])=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of methanesulfonic acid 2-oxo-piperidin-3-yl ester (250 mg, 1/294 mmol, 1.0 eq) and (4-methoxy-phenyl)-piperidin-4-yl-methanone (312 mg, 1.423 mmol, 1.1 eq) in acetonitrile (2.5 mL) was added diisopropylethylamine (351 mg, 0.475 mL, 2.1 eq) and the reaction was heated at 85° C. for 3 hours. The reaction was cooled to room temperature and the solvent evaporated in vacuo. The resulting oily residue was purified by silica gel column chromatography (MeOH/CH2Cl2) to give the title compound as a clear oil (142 mg, 0.449 mmol, 34.7% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.95 (d, J=9.09 Hz, 2H) 7.39-7.43 (br. s, 1H) 7.04 (d, J=8.59 Hz, 2H) 3.84 (s, 3H) 3.23-3.33 (m, 2H) 2.97-3.14 (m, 4H) 2.74-2.85 (m, 2H) 1.75-1.91 (m, 2H) 1.57-1.75 (m, 4H) 1.47-1.54 (m, 2H). MS (m/z, MH+): 316.8

Workup

temperatureThe reaction was cooled to room temperature
customthe solvent evaporated in vacuo
customThe resulting oily residue was purified by silica gel column chromatography (MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-861a0b522ce84a218197971e55220b51
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163003B2

Reaction notes

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