Trifluoroacetic acid → [2-(4-Chlorobenzothiazolyl)][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]methanone

HRID 266090

Reaction equation

HRID 266090 reaction equation
[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH:11]3[CH2:16][CH:15]([CH:17]=[O:18])[CH2:14][CH2:13][NH:12]3)[S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(C(O)=O)(F)(F)F.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35]Br)=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH:11]3[CH2:16][CH:15]([CH:17]=[O:18])[CH2:14][CH2:13][N:12]3[CH2:35][CH2:34][C:31]3[CH:32]=[CH:33][C:28]([O:27][CH3:26])=[CH:29][CH:30]=3)[S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 844271-(2-Bromoethyl)-4-methoxybenzeneHCID 53815766[2-(4-Chlorobenzothiazolyl)](4-piperidinyl)methanone

Product 1

HCID 54412977[2-(4-Chlorobenzothiazolyl)][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Mix [2-(4-chlorobenzothiazolyl)](4-piperidinyl)methanone.CF3CO2H (9.19 mmol), 2-(4-methoxyphenyl)ethyl bromide (2.07 g, 9.64 mmol), potassium carbonate (3.33 g, 24.1 mmol) and dimethylformamide (35 mL) and heat at 90° C. overnight. 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 brine. Dry (MgSO4) and evaporate the solvent in vacuo. Purify by chromatography to give the title compound.

Workup

  1. custompartition between a 2:1 mixture of ethyl acetate/toluene and water
  2. customSeparate the aqueous phase
  3. washwash the organic phase with water and brine
  4. dry with materialDry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. customPurify by chromatography

Sources & evidence

ORD record
ord-8ac0bccc17544f73a370f0721b0c23b8
Source dataset
uspto-grants-1997_07
Patent number
US05650416

Linked notes

Loading…