Triethylamine → HCID 58118601, compound

Temperature

130 °C

A 150 mL pressure vessel was charged with 6-(methoxycarbonyl)-5,6,7,8-tetrahydroquinoline 1-oxide (13.58 g, 65.52 mmol), triethylamine (18 mL, 130 mmol), trimethylsilyl cyanide (26.2 mL, 196 mmol) and acetonitrile (33 mL), and the mixture was heated at 130° C. for 21 h. Slowly quenched reaction into 2M Na2CO3 (250 mL) then diluted with DCM (500 mL). The mixture was filtered through celite and the filter cake washed with DCM (2×200 mL) and water (100 mL). The aqueous layer was extracted with additional DCM (100 mL×2). The combined organics was washed with 1M Na2CO3 (200 mL) and 1 M NaH2PO4 (150 mL×2), dried (Na2SO4), filtered and evaporated. The residue was purified by silica chromatography (100% hexanes to 100% DCM to 20% MeOH in DCM). Additional purification by silica chromatography (0-100% EtOAc in hexanes) yielded a pale yellow solid (3.32 g, 23%). m/z=217.5 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 7.54 (d, J=7.9 Hz, 1H), 7.47 (d, J=7.9 Hz, 1H), 3.74 (s, 3H), 3.18-2.94 (m, 4H), 2.88-2.78 (m, 1H), 2.35-2.26 (m, 1H), 2.09-1.97 (m, 1H).

1. filtrationThe mixture was filtered through celite
2. washthe filter cake washed with DCM (2×200 mL) and water (100 mL)
3. extractionThe aqueous layer was extracted with additional DCM (100 mL×2)
4. washThe combined organics was washed with 1M Na2CO3 (200 mL) and 1 M NaH2PO4 (150 mL×2)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. customevaporated
8. customThe residue was purified by silica chromatography (100% hexanes to 100% DCM to 20% MeOH in DCM)
9. customAdditional purification by silica chromatography (0-100% EtOAc in hexanes)

ORD record

ord-6f09613d4c374ba08d0a16768726a31d

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08153651B2