Triethylamine → HCID 71239712, compound

Temperature

-15 °C

To a solution of 4-(benzyloxy)cyclohexanecarboxylic acid (5.4 g, 23 mmol, 1.0 equiv) and triethylamine (4.82 mL, 34.57 mmol, 1.5 equiv) in DCM (dry, 40 mL) was added ethyl chloroformate (3.0 mL, 31.1 mmol, 1.35 equiv) dropwise between −20 and −10° C. under N2. The white precipitate appeared. The mixture was stirred at about −15° C. for 10 min, dried NH3 was bubbled rapidly into the liquid for 20 min. The mixture was stirred at −15° C. for 30 min, then put into the fridge (−20° C.) overnight. The flask was released the pressure and warm to room temperature. H2O (100 mL) was added. The layer was separated and the aqueous phase was extracted with DCM (3×100 mL). The combined organic solution was washed with brine (50 mL), dried over anhydrous Na2SO4, concentrated to give 5.2 g (96.7%) of 4-(benzyloxy)cyclohexanecarboxamide as a off-white solid.

1. customdried NH3 was bubbled rapidly into the liquid for 20 min
2. stirringThe mixture was stirred at −15° C. for 30 min
3. customput into the fridge (−20° C.) overnight
4. temperaturewarm to room temperature
5. additionH2O (100 mL) was added
6. customThe layer was separated
7. extractionthe aqueous phase was extracted with DCM (3×100 mL)
8. washThe combined organic solution was washed with brine (50 mL)
9. dry with materialdried over anhydrous Na2SO4
10. concentrationconcentrated

ORD record

ord-bb5d09f9f3984a20b1bdf23031a2cc74

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09226923B2