Diethylamine → N,N-diethyl-2-oxo-2-(4-oxo-cyclohexyl)-acetamide

Compound 13 was synthesized starting from treating oxo-(4-oxo-cyclohexyl)-acetic acid with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (2 eq.) and 4-dimethylaminopyridine (catalytic amount) in DMF. After stirring at room temperature for approximately 10 min., the reaction mixture was cooled in an ice-bath and diethylamine (1.5 eq.) was added. The resulting mixture was stirred at room temperature for 5 hours with TLC monitoring. The solvent was removed by evaporation. The residue was diluted with EtOAc and washed with H2O twice. The aqueous then was extracted with EtOAc and the organic layer was dried over Na2SO4. The desired intermediate N,N-diethyl-2-oxo-2-(4-oxo-cyclohexyl)-acetamide was obtained after purification through a combiflash chromatography system using a silica gel cartridge and CH2Cl2/MeOH gradient eluent, which further condensed with 3-hydroxybenzaldehyde (2.5 eq.) by following the same procedure described above to get the desired product as a yellow solid ESI MS m/z: 406.51 [M+H]+; 1H NMR (300 MHz, DMSO-d6) δ: 7.54 (s. 2H, benzylidene CH═), 7.25 (t, 2H, J=7.8 Hz, aromatic ring H), 6.93-6.89 (m, 4H, aromatic ring H), 6.81-6.78 (m, 2H, aromatic ring H), 3.23 (q, 4H, J=7.2 Hz, —NCH2CH3), 2.95 (m, 4H, 4-oxo-cyclohexyl-H-2, 6), 2.54 (m, 1H, cyclohexyl-H-1), 0.94 (m, 6H, —NCH2CH3).

1. customCompound 13 was synthesized
2. temperaturethe reaction mixture was cooled in an ice-bath
3. stirringThe resulting mixture was stirred at room temperature for 5 hours with TLC monitoring
4. customThe solvent was removed by evaporation
5. additionThe residue was diluted with EtOAc
6. washwashed with H2O twice
7. extractionThe aqueous then was extracted with EtOAc
8. dry with materialthe organic layer was dried over Na2SO4

ORD record

ord-a545c7ab5b95492fa061651ed11f2389

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822732B2