Ethyl trifluoroacetate → Acetamide, N-(2-aminocyclohexyl)-2,2,2-trifluoro-, cis-

HRID 2092862

Reaction equation

HRID 2092862 reaction equation
[C@@H:1]1([NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][C@@H:2]1[NH2:7].[F:9][C:10]([F:17])([F:16])[C:11](OCC)=[O:12]>CCO>[NH2:7][C@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C@H:1]1[NH:8][C:11](=[O:12])[C:10]([F:17])([F:16])[F:9]

Participants

4

Procedure

cis-Cyclohexane-1,2-diamine (5.00 g, 43.9 mmol, 1.00 eq) was charged to a 250 mL three-neck round bottom flask equipped with an overhead stirrer and a thermocouple. Ethanol (50 mL) was added and the solution was cooled to <0° C. using an ice-brine bath. A solution of ethyl trifluoroacetate (6.23 g, 1.00 eq) in EtOH (25 mL) was added via a syringe pump over a one hour period. Once the addition was complete, the cooling bath was removed and the solution was slowly warmed to RT and stirred for 3.5 hours to afford the title compound in EtOH. Half (41 mL, about 21.9 mmol) of the total solution (about 82 mL) was carried into the next step.

Workup

  1. customequipped with an overhead stirrer
  2. temperaturethe solution was cooled to <0° C.
  3. additionOnce the addition
  4. customthe cooling bath was removed

Sources & evidence

ORD record
ord-eccf39775a9b415b9741c6b119369bd0
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Linked notes

Loading…