Hydrochloric Acid → HCID 57591499, compound

HRID 1784143Notes

Reaction equation

HRID 1784143 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12](=O)[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.Cl>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:21])([F:23])[F:22])=[CH:16][CH:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 51272493N-(3,4-Dimethoxy-phenyl)-2-(4-trifluoromethyl-phenyl)-acetamide

Product 1

HCID 57591499HCID 57591499, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3 g (8.8 mmol) N-(3,4-Dimethoxy-phenyl)-2-(4-trifluoromethyl-phenyl)-acetamide and 1 g (26.3 mmol) LiAlH4 in 100 mL THF was stirred for 1 h at room temperature. Water and HCl aq. was added and the mixture was extracted with ethyl acetate. The combined organic phases were washed with water, dried with MgSO4 and evaporated to dryness. The residue was purified by flash column chromatography on silica eluting with a gradient formed from ethyl acetate and heptane. The product containing fractions were combined and evaporated to dryness to yield 0.7 g (24%) of the title compound. MS(m/e): 326.1 (MH+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic phases were washed with water
  3. dry with materialdried with MgSO4
  4. customevaporated to dryness
  5. customThe residue was purified by flash column chromatography on silica eluting with a gradient
  6. customformed from ethyl acetate and heptane
  7. additionThe product containing fractions
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-8e68a2667e8044979cef6c0524dbcd71
Source dataset
uspto-grants-2009_03
Patent number
US07501541B2

Reaction notes

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