Hydrochloric Acid → HCID 178479758, compound

Temperature

70 °C

Phosgene (50 mmol of a 20% w/w solution in toluene) was added to N,N-dimethylformamide (3.9 mL, 50 mmol) with stirring in an ice bath over 5 min to give a white paste. This mixture was allowed to stand until no further gas evolution was observed (˜30 min). Methyl 7,7-dimethoxyheptanoate (5.1 g, 25 mmol), prepared from cycloheptene following a published method (Claus, R. E., and Schreiber, S. L. (1986) Ozonolytic cleavage of cyclohexene to terminally differentiated products: methyl 6-oxohexanoate, 6,6-dimethoxyhexanal, methyl 6,6-dimethoxyhexanoate. Organic Syntheses 64, 150-156.), was then added dropwise to the reaction solution followed by heating at 70° C. for 1 hour. After cooling, the solvent was removed by rotary evaporation giving a yellow-brown oil. The oil was suspended in water (20 mL) then 5 mL of 10% aqueous HCl and aniline hydrochloride (6.5 g, 50 mmol) were added. The resulting mixture was sealed in a thick-walled glass pressure tube and heated at 120° C. in an oil bath for 1.5 hours. After heating, the reaction solution was cooled slowly to room temperature over 2 hours, during which the product crystallized (if the reaction is cooled too quickly, a sticky precipitate is formed instead). After filtration and washing with water, 1 is obtained as a yellow solid (2.05 g, 23%). 1H NMR (400 MHz, DMSO-d6): δ 8.72 (d, 2H, J=12 Hz), 7.58 (d, 4H, J=8.4 Hz), 7.51 (t, 4H, J=8.0 Hz), 7.30 (t, 4H, J=7.2 Hz), 2.77 (t, 2H, J=6.4 Hz), 2.27 (t, 2H, J=7.6 Hz), 1.71-1.64 (m, 2H), 1.50-1.42 (m, 2H). HRMS-ESI [M]+ m/z calcd. for [C20H23N2O2]+ 323.1754, found 323.1743.

1. customto give a white paste
2. custom(˜30 min)
3. addition), was then added dropwise to the reaction solution
4. temperatureAfter cooling
5. customthe solvent was removed by rotary evaporation
6. customgiving a yellow-brown oil
7. customThe resulting mixture was sealed in a thick-walled glass pressure tube
8. temperatureheated at 120° C. in an oil bath for 1.5 hours
9. temperatureAfter heating
10. temperaturethe reaction solution was cooled slowly to room temperature over 2 hours, during which the product
11. customcrystallized (if the reaction
12. temperatureis cooled too quickly
13. customa sticky precipitate is formed instead)
14. filtrationAfter filtration
15. washwashing with water

ORD record

ord-45b6b38848804d64b0688193b52c2daf

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916137B2