2-{6-Methoxy-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-benzaldehyde → 1-{2-[4-(10-methoxy-5H,7H-6-oxa-12-thia-dibenzo[a,e]azulen-7-yl)-phenoxy]-ethyl)-piperidine

HRID 916857Notes

Reaction equation

HRID 916857 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:16]([C:17](=[O:33])[C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)=[CH:20][CH:19]=3)=[C:15]([C:34]3[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=3[CH:36]=O)[S:14][C:13]=2[CH:42]=1>C1COCC1>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:16]3[CH:17]([C:18]4[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][N:27]5[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]5)=[CH:22][CH:23]=4)[O:33][CH2:36][C:35]4[CH:38]=[CH:39][CH:40]=[CH:41][C:34]=4[C:15]=3[S:14][C:13]=2[CH:42]=1

Participants

4

Reactant 2

HCID 179870572-{6-Methoxy-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-benzaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 100968891-{2-[4-(10-methoxy-5H,7H-6-oxa-12-thia-dibenzo[a,e]azulen-7-yl)-phenoxy]-ethyl)-piperidineYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add LAH solution (1M/THF) to a solution of 2-{6-methoxy-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-benzaldehyde (410 mg, 0.82 mmol) in THF (5 mL) at r.t. until LCMS analysis indicates complete consumption of starting material. Dilute the mixture with THF (10 mL) and water (2 mL), followed by cautious addition of HCl(5 M) to pH 1. Heat gently for 10 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 1-{2-[4-(10-methoxy-5H,7H-6-oxa-12-thia-dibenzo[a,e]azulen-7-yl)-phenoxy]-ethyl}-piperidine (266 mg, 67%).

Workup

  1. customconsumption of starting material
  2. additionDilute the mixture with THF (10 mL) and water (2 mL)
  3. additionfollowed by cautious addition of HCl(5 M) to pH 1
  4. temperatureHeat gently for 10 min
  5. additionDilute with CH2Cl2
  6. customquench with aq. NaHCO3
  7. washWash the organic phase with water and brine
  8. dry with materialdry over MgSO4
  9. filtrationfilter
  10. concentrationconcentrate
  11. customPurify the crude product by flash chromatography (0-10% (2M NH3 in MeOH)/CH2Cl2)

Sources & evidence

ORD record
ord-dbe0e6d0d191434687b79260d1f15109
Source dataset
uspto-grants-2007_09
Patent number
US07271264B2

Reaction notes

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