Water → {1-[2,4-Bis(trifluoromethyl)benzyl]azepan-4-yl}methanol

HRID 1620561Notes

Reaction equation

HRID 1620561 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][OH:9])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:19]=1[C:28]([F:31])([F:30])[F:29].O>CN(C=O)C>[F:29][C:28]([F:30])([F:31])[C:19]1[CH:20]=[C:21]([C:24]([F:27])([F:25])[F:26])[CH:22]=[CH:23][C:18]=1[CH2:17][N:1]1[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][OH:9])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5188712,4-Bis(trifluoromethyl)benzyl bromideHCID 22594076(Azepan-4-yl)methanol

Product 1

HCID 86678740{1-[2,4-Bis(trifluoromethyl)benzyl]azepan-4-yl}methanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of azepan-4-ylmethanol (1.40 g) and potassium carbonate (3.00 g) in DMF (54.2 mL) was added 1-(bromomethyl)-2,4-bis(trifluoromethyl)benzene (2.03 mL). The reaction mixture was stirred at room temperature overnight, poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.901 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ef286390e12145fcab00f9f8e66b1024
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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