Diethyl Ether → (cis)-2-amino-N-(2,2,2-trifluoroethyl)cyclohexanecarboxamide Hydrochloride

HRID 510183Notes

Reaction equation

HRID 510183 reaction equation
[F:1][C:2]([F:22])([F:21])[CH2:3][NH:4][C:5]([C@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[NH:13]C(=O)OC(C)(C)C)=[O:6].[ClH:23].O1CCOCC1.C(OCC)C.CCOCC.CCCCCC>O1CCOCC1>[ClH:23].[NH2:13][C@H:8]1[CH2:9][CH2:10][CH2:11][CH2:12][C@H:7]1[C:5]([NH:4][CH2:3][C:2]([F:1])([F:21])[F:22])=[O:6]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 204431481,4-Dioxane hydrochlorideHCID 21584099Diethylether hexaneHCID 97027465Tert-butyl{(cis)-2-[(2,2,2-trifluoroethyl)carbamoyl]cyclohexyl}carbamate

Product 1

HCID 117628534(cis)-2-amino-N-(2,2,2-trifluoroethyl)cyclohexanecarboxamide Hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To tert-butyl {(cis)-2-[(2,2,2-trifluoroethyl)carbamoyl]cyclohexyl}carbamate, I-5a (2.55 g, 7.86 mmol) in Dioxane (10 ml) was added 4 M HCl/Dioxane (19.66 ml, 79 mmol) and the mixture allowed to stir at RT for 60 min. The reaction was concentrated in vacuo and resulting solid slurried with diethyl ether (100 mL). Re-concentration of the mixture and re-slurry of the solid with ether/hexane gave a free flowing solid. Final concentration of the mixture gave a white solid, I-5b, (2.1 gm) which was stored under nitrogen.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customresulting solid
  3. customFinal concentration of the mixture gave a white solid

Sources & evidence

ORD record
ord-23ac0915210640fc89faf0c5e91f373e
Source dataset
uspto-grants-2015_08
Patent number
US09096598B2

Reaction notes

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