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

HRID 1249574Notes

Reaction equation

HRID 1249574 reaction equation
[C:1]1([C:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].C(O)C>[C:29]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH:9]2[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[CH2:13][CH2:14]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 1

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

Product 1

HCID 137545473-[8-[4-(2,2-Diphenylethyl)-1-piperidinyl]octyl]pyridineYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The title compound was prepared by the hydrogenation of 7.3 g of 3-[8-[4-(2,2-diphenylethenyl)-1-piperidinyl]octyl]pyridine at ambient conditions using 100 mL of ethanol and 1.5 g of 10% palladium on carbon catalyst. After filtration and evaporation, the residue was crystallized from hexane to give 6.0 g (82%) of 3-[8-[4-(2,2-diphenylethyl)-1-piperidinyl]octyl]pyridine, mp 68°-70° C. Analysis Calculated for C32H42N2 : C, 84.53: H, 9.31; N, 6.16. Found: C, 84.68; H, 9.15; N, 6.12. The fumarate salt was crystallized from acetone, mp 110°-111° C. Analysis Calculated for C32H42N2.C4H4O4 : C, 75.76; H, 8.12; N, 4.91. Found: C, 75.59; H, 8.00; N, 4.83.

Workup

  1. filtrationAfter filtration and evaporation
  2. customthe residue was crystallized from hexane

Sources & evidence

ORD record
ord-fc5f4f1e7b6042e3906235a1cd558539
Source dataset
uspto-grants-1986_12
Patent number
US04632925

Reaction notes

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