Sodium Iodide → HCID 20223430, compound

HRID 1249578Notes

Reaction equation

HRID 1249578 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1.[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][CH:9]2[CH2:10][CH2:11][N:12]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH:32]3[CH2:37][CH2:36][CH2:35][NH:34][CH2:33]3)[CH2:13][CH2:14]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 11608538HCID 11608538, compoundHCID 13754500HCID 13754500, compound

Product 1

HCID 20223430HCID 20223430, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared in a manner similar to that employed for the compound of Example 23 starting with 6.59 g of 4-(2,2-diphenylethenyl)piperidine, 6.4 g of 3-(10-chlorodecyl)pyridine, 3.75 g of sodium iodide, 2.65 g of anhydrous sodium carbonate, and 40 mL of dimethylformamide. The mixture was heated at 75° for 18 hours and the solvent was evaporated. The residue was partitioned between 1N sodium hydroxide and ethyl acetate and the organic layer was removed, dried over sodium sulfate, decolorized with charcoal, filtered, and evaporated to give 10.4 g (86%) of product as a colorless oil. Crystallization from hexane provided the pure 3-[10-[4-(2,2-Diphenylethenyl)-1-piperidinyl]decyl]pyridine, mp 63°-65° C. Analysis Calculated for C34H44N2 : C, 84.95; H, 9.23; N, 5.83. Found: C. 85.21; H 9.27; N, 5.84. The fumaric acid salt was obtained from acetone, mp 134°-136° C. Analysis Calculated for C34H44N2.C4H4O4 : C, 76.48; H, 8.11; N, 4.69. Found: C, 76.53; H, 8.17; N, 4.88.

Workup

  1. temperatureThe mixture was heated at 75° for 18 hours
  2. customthe solvent was evaporated
  3. customThe residue was partitioned between 1N sodium hydroxide and ethyl acetate
  4. customthe organic layer was removed
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-4b6d1fb0adb74f53ad402b9ddaa5af46
Source dataset
uspto-grants-1986_12
Patent number
US04632925

Reaction notes

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