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

HRID 1249573Notes

Reaction equation

HRID 1249573 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][C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=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][C:30]3[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=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 13754500HCID 13754500, compoundHCID 137545053-(8-Chlorooctyl)pyridine

Product 1

HCID 137545063-[8-[4-(2,2-Diphenylethenyl)-1-piperidinyl]octyl]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

The title compound was prepared in a manner similar to that employed for the compound of Example 23 above starting with 8.64 g of 4-(2,2-diphenylethenyl)piperidine, 7.4 g of 3-(8-chlorooctyl)pyridine, 4.92 g of sodium iodide, 3.48 g of sodium carbonate, and 50 mL of dimethylformamide. The mixture was stirred an heated at 75° C. for 18 hours and then evaporated to dryness. The residue was partitioned between ethyl acetate and 1N sodium hydroxide and the organic layers were dried over sodium sulfate and evaporated to give 11.0 g (74%) of crude free base. Recrystallization from hexane gave the analytically pure, 3-[8-[4-(2,2-diphenylethenyl)-1-piperidinyl]octyl]pyridine, mp 54°-55° C. Analysis Calculated for C32H40N2 : C, 84.91; H, 8.91; N, 6.19. Found: C, 84.81; H, 8.74; N, 6.14. The fumaric acid salt was crystallized from ethanol/acetone, mp 128° -129° C. Analysis Calculated for C32H40N2.C4H4O4 : C, 76.02; H, 7.80; N, 4.93. Found: C, 76.15, H, 7.79, N, 4.89.

Workup

  1. customThe title compound was prepared in a manner similar to
  2. customevaporated to dryness
  3. customThe residue was partitioned between ethyl acetate and 1N sodium hydroxide
  4. dry with materialthe organic layers were dried over sodium sulfate
  5. customevaporated
  6. customto give 11.0 g (74%) of crude free base
  7. customRecrystallization from hexane

Sources & evidence

ORD record
ord-bbc43523a83543d1816eb6d9668c8896
Source dataset
uspto-grants-1986_12
Patent number
US04632925

Reaction notes

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