Hydrochloric Acid → 2-{6-Methoxy-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-benzaldehyde

HRID 916856Notes

Reaction equation

HRID 916856 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[S:16][C:15]2[CH:17]=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:14]=2[C:13]=1[C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)=[CH:27][CH:26]=1)=[O:24].Cl.O>C1COCC1.C(Cl)Cl>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:14]2[C:13]([C:23](=[O:24])[C:25]3[CH:26]=[CH:27][C:28]([O:31][CH2:32][CH2:33][N:34]4[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]4)=[CH:29][CH:30]=3)=[C:12]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[CH:2]=[O:1])[S:16][C:15]=2[CH:17]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 17987059[2-(2-[1,3]Dioxolan-2-yl-phenyl)-6-methoxy-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

Product 1

HCID 179870572-{6-Methoxy-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-benzaldehyde

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [2-(2-[1,3]dioxolan-2-yl-phenyl)-6-methoxy-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (crude) in THF (15 mL), add HCl (2 mL, 5M) and water (2 mL). Heat the mixture to reflux for 30 min. Dilute with CH2Cl2 and quench with aq. NaHCO3. Wash the organic phase with water and brine, dry over MgSO4, filter and concentrate. Purify the crude product by flash chromatography (0-10% (2M NH3 in MeOH)/CH2Cl2) to afford 2-{6-methoxy-3-[4(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-benzaldehyde (410 mg) which is contaminated with unidentified byproducts and is used without further purification.

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux for 30 min
  3. customquench with aq. NaHCO3
  4. washWash the organic phase with water and brine
  5. dry with materialdry over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify the crude product by flash chromatography (0-10% (2M NH3 in MeOH)/CH2Cl2)

Sources & evidence

ORD record
ord-22293cc7e9604755ab8c0c19252e6728
Source dataset
uspto-grants-2007_09
Patent number
US07271264B2

Reaction notes

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