4-Methylmorpholine → 4,4-Difluorocyclohexanecarboxamide

HRID 1483786Notes

Reaction equation

HRID 1483786 reaction equation
[F:1][C:2]1([F:11])[CH2:7][CH2:6][CH:5]([C:8](O)=[O:9])[CH2:4][CH2:3]1.C[N:13]1CCOCC1.CC(COC(Cl)=O)C.[OH-].[NH4+]>C1COCC1>[F:1][C:2]1([F:11])[CH2:7][CH2:6][CH:5]([C:8]([NH2:13])=[O:9])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 14923Ammonium HydroxideHCID 62365Isobutyl chloroformateHCID 27791364,4-Difluorocyclohexanecarboxylic acid

Product 1

HCID 469422314,4-DifluorocyclohexanecarboxamideYield 53.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 4,4-difluorocyclohexanecarboxylic acid (3.5 g, 21 mmol) in 80 mL THF, 4-methylmorpholine (2.51 g, 21 mmol) was added at −70° C., followed by isobutyl chloridocarbonate (2.85 g, 21 mmol). 30 min later, 10 mL ammonium hydroxide was added. The resulting mixture was allowed to warm up to 0° C. After removal of all solvents, the residue was washed with water, PE to afford the compound 4,4-difluorocyclohexanecarboxamide (1.82 g, 40%) as a white solid.

Workup

  1. customAfter removal of all solvents
  2. washthe residue was washed with water, PE

Sources & evidence

ORD record
ord-2174b11f6a2345ac992642fda24bab23
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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