Triethylamine → HCID 178501230, compound

Temperature

0 °C

To a stirred suspension of trans-4-amino-cyclohexylcarboxylic acid methyl ester hydrochloride (6.7 g, 34.7 mmol) in dry THF (90 ml) under nitrogen atmosphere was added triethylamine (12 ml, 86.8 mmol). The suspension was cooled to 0° C. and 2-chloro-5-(trifluoromethyl)benzoyl chloride (8.85 g, 36.4 mmol) in dry THF (40 ml) was added dropwise over 20 minutes. The resulting thick, colourless slurry was stirred at 0-5° C. for 30 minutes and then allowed to warm to room temp and stirred at room temp for 1 hour. The reaction was quenched by the dropwise addition of water (5 ml) in THF (45 ml) to give a clear solution. This was diluted with water (100 ml) and ethyl acetate (300 ml). The biphasic mixture was stirred for 5 minutes then the organic phase was separated and washed successively with water (100 ml), saturated sodium bicarbonate (100 ml) and saturated brine (100 ml), dried (MgSO4), filtered and evaporated to give a colourless solid; [M+H]+364.

1. temperatureto warm to room temp
2. stirringstirred at room temp for 1 hour
3. customThe reaction was quenched by the dropwise addition of water (5 ml) in THF (45 ml)
4. customto give a clear solution
5. stirringThe biphasic mixture was stirred for 5 minutes
6. customthe organic phase was separated
7. washwashed successively with water (100 ml), saturated sodium bicarbonate (100 ml) and saturated brine (100 ml)
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. customevaporated
11. customto give a colourless solid

ORD record

ord-8694fbc0b8c741308cc3c3315d7e00b5

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08835444B2