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

HRID 711561

Reaction equation

HRID 711561 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-62478a3501d04b30ba976b92bb573c84
Source dataset
uspto-grants-2015_11
Patent number
US09181255B2

Linked notes

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