Water → 2,2,2-Trifluoro-N-(4-hydroxycyclohexyl)-N-methylacetamide

HRID 2402598Notes

Reaction equation

HRID 2402598 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([NH:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([OH:12])[CH2:8][CH2:7]1)=[O:4].[H-].[Na+].I[CH3:18].O>CC(N(C)C)=O>[F:1][C:2]([F:13])([F:14])[C:3]([N:5]([CH:6]1[CH2:7][CH2:8][CH:9]([OH:12])[CH2:10][CH2:11]1)[CH3:18])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178523812HCID 178523812, compound

Product 1

HCID 584681842,2,2-Trifluoro-N-(4-hydroxycyclohexyl)-N-methylacetamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
0 °C

Procedure

5 g of 2,2,2-trifluoro-N-(4-hydroxy-cyclohexyl)-acetamide (148) were dissolved in 25 mL of dimethyl acetamide, 625 mg of 95% sodium hydride were added and the reaction mixture was cooled to 0° C. 1.64 mL of iodomethane were added slowly and the reaction mixture was allowed to warm to room temperature. Upon completion, the reaction mixture was poured into water, extracted three times with methyl tert.butyl ether and the combined organic layer was extracted once with brine, dried over sodium sulfate and evaporated to dryness. The residue was taken up in water and lyophilized to remove remainders of dimethyl acetamide to yield 4.0 g of product. Rt=0.95 min (Method C). Detected mass: 226.2 (M+H+).

Workup

  1. temperatureto warm to room temperature
  2. extractionextracted three times with methyl tert.butyl ether
  3. extractionthe combined organic layer was extracted once with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customto remove remainders of dimethyl acetamide

Sources & evidence

ORD record
ord-0ed1dcdc049a4464b6aceb67bc9b25ed
Source dataset
uspto-grants-2014_08
Patent number
US08796458B2

Reaction notes

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