Triphosgene → HCID 20356910, compound

Temperature

40 °C

To a solution of triphosgene (0.22 g, 0.33 eq.) in CH2Cl2 was added 3-methane-sulfonyl-phenylamine hydrochloride (0.5 g, 2.4 mmol), followed by the dropwise addition of TEA (0.37 ml, 1.1 eq.). The mixture was heated to 40° C. for 30 min. It was allowed to cool to rt and stirred for an additional 45 min. The isocyanate solution was then added to a solution of 2-[3-(4-chlorobenzyl)-8-aza-bicyclo[3.2.1]oct-8-yl]-1-methyl-ethylamine (0.18 g, 0.6 mmol) (prepared according to the procedure described in example 4, steps 1 to 4) in 6 ml of CH2Cl2. The mixture was stirred overnight at rt. It was diluted with CH2Cl2 and the organic layer was washed with Na2CO3 (sat.) twice, NaCl (sat.) and dried over Na2SO4. The crude mixture was purified on a silica-gel column with 1% iPrNH2, 9% MeOH in EtOAc to give 55% of Example 5 (M+: 490).

1. temperatureto cool to rt
2. customprepared
3. stirringThe mixture was stirred overnight at rt
4. washthe organic layer was washed with Na2CO3 (sat.) twice
5. dry with materialNaCl (sat.) and dried over Na2SO4
6. customThe crude mixture was purified on a silica-gel column with 1% iPrNH2, 9% MeOH in EtOAc

ORD record

ord-23f198ef4e9e47f1a2a8dd10acbcbbba

Source dataset

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07081531B2