Trifluoroacetic acid → [Benzo[b]thiophene-3-yl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]methanone

HRID 1491678

Reaction equation

HRID 1491678 reaction equation
[S:1]1[CH:5]=[C:4]([C:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[O:7])[C:3]2[CH:14]=[CH:15][CH:16]=[CH:17][C:2]1=2.C(C(O)=O)(F)(F)F.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34]Br)=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[S:1]1[CH:5]=[C:4]([C:6]([CH:8]2[CH2:9][CH2:10][N:11]([CH2:34][CH2:33][C:30]3[CH:31]=[CH:32][C:27]([O:26][CH3:25])=[CH:28][CH:29]=3)[CH2:12][CH2:13]2)=[O:7])[C:3]2[CH:14]=[CH:15][CH:16]=[CH:17][C:2]1=2

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 844271-(2-Bromoethyl)-4-methoxybenzeneHCID 15337457(Benzo[b]thiophene-3-yl)(4-piperidinyl)methanone

Product 1

HCID 9799982[Benzo[b]thiophene-3-yl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Mix (benzo[b]thiophene-3-yl)(4-piperidinyl)methanone.CF3CO2H (2.0 g, 5.56 mmol), 2-(4-methoxyphenyl)ethyl bromide (1.27 g, 5.93 mmol ), potassium carbonate (1.95 g, 1.41 mmol) and anhydrous dimethylformamide (20 mL). Warm to approximately 90° C. and stir overnight. Allow to cool to room temperature and partition between a 2:1 mixture of ethyl acetate: toluene and water. Separate the aqueous phase and wash the organic phase with water and saturated sodium chloride. Dry (Na2SO4) and evaporate the solvent Purify by chromatography (40% ethyl acetate/hexane) and recrystallize (cyclohexane) to give the title compound pale yellow plates; mp 114°-116° C.

Workup

  1. temperatureto cool to room temperature
  2. custompartition between a 2:1 mixture of ethyl acetate
  3. customSeparate the aqueous phase
  4. washwash the organic phase with water and saturated sodium chloride
  5. dry with materialDry (Na2SO4)
  6. customevaporate the solvent
  7. customPurify by chromatography (40% ethyl acetate/hexane)
  8. customrecrystallize (cyclohexane)

Sources & evidence

ORD record
ord-889570dc210d4762a0c7ac4adf099917
Source dataset
uspto-grants-1994_12
Patent number
US05371093

Linked notes

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