Potassium Carbonate → HCID 15870514, compound

HRID 1600594Notes

Reaction equation

HRID 1600594 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[S:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[C:10]=2[O:18][C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)[CH:6]=[CH:7][CH:8]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>CN(C=O)C>[N:35]1([CH2:34][CH2:33][O:25][C:22]2[CH:21]=[CH:20][C:19]([O:18][C:10]3[C:11]4[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=4[S:13][C:9]=3[C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)=[CH:24][CH:23]=2)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 748271-(2-Chloroethyl)piperidineHCID 15870513HCID 15870513, compound

Product 1

HCID 15870514HCID 15870514, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(3-methoxyphenyl)-3-(4-hydroxyphenoxy)benzo[b]thiophene (3.27 g, 9.40 mmol) in 200 mL of anhydrous DMF was added finely ground anhydrous K2CO3 (13.0 g, 94 mmol) and 2-chloroethylpiperidine (2.40 g, 14.1 mmol). The resulting solution was stirred under N2 at room temperature for 16 h. The reaction was then partitioned between EtOAc and H2O. The layers were separated and the organic was washed several times with H2O. The organic was dried (Na2SO4) and concentrated in vacuo to an oil that was chromatographed (SiO2, 0-5% CH3OH/CHCl3) to provide 3-[4-[2-(1-piperidinyl)ethoxy]phenoxy]-2-(3-methoxyphenyl)benzo[b]thiophene as a brown oil. This material was treated with Et2O.HCl to provide 2.0 g (43%) 3-[4-[2-(1-piperidinyl)ethoxy]phenoxy]-2-(3-methoxyphenyl)benzo[b]thiophene hydrochloride as a white solid.

Workup

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

Sources & evidence

ORD record
ord-908a97ff66224d9d88501e66412c0172
Source dataset
uspto-grants-1999_11
Patent number
US05977098

Reaction notes

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