Sodium Iodide → 3-[8-[4-[2,2-Bis(3-methoxyphenyl)ethenyl]-1-piperidinyl]octyl]pyridine

HRID 1249587Notes

Reaction equation

HRID 1249587 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)=[CH:10][CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:6]=[CH:7][CH:8]=1.Cl[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=1.[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH3:24][O:23][C:19]1[CH:18]=[C:17]([C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:10][CH:11]2[CH2:16][CH2:15][N:14]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]3[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=3)[CH2:13][CH2:12]2)[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 137545014-[2,2-Bis(3-methoxyphenyl)ethenyl]piperidineHCID 137545053-(8-Chlorooctyl)pyridine

Product 1

HCID 137545083-[8-[4-[2,2-Bis(3-methoxyphenyl)ethenyl]-1-piperidinyl]octyl]pyridineYield 70.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-[2,2-bis(3-methoxyphenyl)ethenyl]piperidine (1.65 g), 3-(8-chloroctyl)pyridine (1.13 g), sodium iodide (0.75 g) and anhydrous sodium carbonate (0.53 g) in dimethylformamide (10 ml) was stirred under argon at 75° for 16 hours. The solvent was removed in vacuo and the residue was taken up in a mixture of ethyl acetate and 1N sodium hydroxide solution. The separated aqueous layer was reextracted with three portions of ethyl acetate. The organic layers were washed in turn with water and brine, then were combined, dried over sodium sulfate, decolorized with charcoal and evaporated to give 2.5 g of crude product as an oil. The oil was purified by HPLC (hexane:ethyl acetate:triethylamine; 34:17:1) to give 1.8 g of 3-[8-[4-[2,2-bis(3-methoxyphenyl)ethenyl]-1-piperidinyl]octyl]pyridine, as an oil.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was taken up in a mixture of ethyl acetate and 1N sodium hydroxide solution
  3. washThe organic layers were washed in turn with water and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto give 2.5 g of crude product as an oil
  7. customThe oil was purified by HPLC (hexane:ethyl acetate:triethylamine; 34:17:1)

Sources & evidence

ORD record
ord-da10b2eae2bf4e48bb4269013bf68395
Source dataset
uspto-grants-1986_12
Patent number
US04632925

Reaction notes

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