Hydrochloric Acid → HCID 46832035, compound

Temperature

22.5 °C

To a solution of 1H-benzo[d][1,2,3]triazole (0.238 g, 2 mmol) in dry DCM (5 ml) was added at 0-5° C. 20% solution of phosgene (1.052 ml, 2.000 mmol) in toluene. The mixture was stirred for 30 min at 20-25° C., cooled to 0-5° C., triethylamine (0.279 ml, 2.000 mmol) was added with stirring. The suspension was diluted with dry DCM (5 ml), solid (R)-quinuclidin-3-amine dihydrochloride (0.398 g, 2.000 mmol) and triethylamine (0.836 ml, 6.00 mmol) added at 0-5° C. The mixture was allowed to warm up to 20-25° C. during 30 min, diluted with 2-propanol, evaporated to dryness. The residue was distributed between water (15 ml) and DCM (15 ml), organic phase dried (MgSO4), concentrated, separated on a column (DCM-MeOH 9:1), fractions collected to give oil. The oil dissolved in ether with minimum of DCM, the solution acidified with 2M HCl in ether to pH 1-2, the precipitate collected, washed with ether, dried in vacuum at 45° C. Yield 0.12 g (19.5%).

1. temperaturecooled to 0-5° C.
2. stirringwith stirring
3. additionadded at 0-5° C
4. temperatureto warm up to 20-25° C. during 30 min
5. customevaporated to dryness
6. dry with materialdried (MgSO4)
7. concentrationconcentrated
8. customseparated on a column (DCM-MeOH 9:1), fractions
9. customcollected
10. customto give oil
11. customthe precipitate collected
12. washwashed with ether
13. customdried in vacuum at 45° C

ORD record

ord-029e2b1dac724d98852164a22a1d93c3

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353082B2