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

HRID 2173045

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

Conditions

Temperature: -5 °C

Procedure

To a 12-L 4-neck cylindrical jacketed vessel equipped with an overhead stirrer, J-KEM thermocouple, and an addition funnel, was charged a solution of cis-cyclohexane-1,2-diamine (500.0 g, 4.378 mole) in EtOH (2.5 L) under nitrogen. The vessel was cooled to −5° C. Ethyl trifluoroacetate (521 mL, 1.00 eq, Acros lot #A0267844) was charged to the addition funnel and was added dropwise to the reaction mixture over a period of 1 hour and 45 minutes to afford the title compound in EtOH, which was carried forward into the next step.

Workup

customTo a 12-L 4-neck cylindrical jacketed vessel equipped with an overhead stirrer
additionwas added dropwise to the reaction mixture over a period of 1 hour and 45 minutes

Sources & evidence

ORD record: ord-fe73bf6f550141938311e04c4807b115
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056873B2

Linked notes

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