Potassium Carbonate → HCID 69821644, compound

HRID 1602923Notes

Reaction equation

HRID 1602923 reaction equation
[OH:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[C:8]3[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=3[S:10][C:11]=2[CH:12]([CH3:14])[CH3:13])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>CN(C=O)C>[N:30]1([CH2:29][CH2:28][O:1][C:2]2[CH:3]=[CH:4][C:5]([O:6][C:7]3[C:8]4[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=4[S:10][C:11]=3[CH:12]([CH3:14])[CH3:13])=[CH:19][CH:20]=2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 748271-(2-Chloroethyl)piperidineHCID 19608552HCID 19608552, compound

Product 1

HCID 69821644HCID 69821644, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[(4-hydroxy)phenoxy]-2-(isopropyl)benzo[b]thiophene (1.71 g, 6.0 mmol) in 100 mL of anhydrous DMF is added finely ground anhydrous K2CO3 (8.30 g, 60 mmol) and 2-chloroethylpiperidine (1.54 g, 9.0 mmol). The resulting solution is stirred under N2 at room temperature for 16 h. The reaction is then partitioned between EtOAc and H2O. The layers are separated and the organic is washed several times with H2O. The organic is dried (Na2SO4) and concentrated in vacuo to an oil that is chromatographed (SiO2, 0-5% CH3OH/CHCl3) to provide [3-[4-[2-(1-piperidinyl)ethoxy]phenoxy]-2-(isopropyl]benzo[b]thiophene as a brown oil. This material is treated with Et2OoHCl to provide 1.27 g (54%) of [3-[4-[2-(1-piperidinyl)ethoxy]phenoxy]-2-(isopropyl]benzo[b]thiophene hydrochloride as a white solid.

Workup

  1. customThe reaction is then partitioned between EtOAc and H2O
  2. customThe layers are separated
  3. washthe organic is washed several times with H2O
  4. dry with materialThe organic is dried (Na2SO4)
  5. concentrationconcentrated in vacuo to an oil that
  6. customis chromatographed (SiO2, 0-5% CH3OH/CHCl3)

Sources & evidence

ORD record
ord-2c0d58e817fd4062b618883fc366adb3
Source dataset
uspto-grants-1999_11
Patent number
US05985897

Reaction notes

Loading…