3-Pyridinebutanoic acid → 4-[2,2-Bis[4-fluorophenyl)ethenyl]1-[1-oxo-4-(3-pyridinyl)butyl]piperidine

HRID 1249569Notes

Reaction equation

HRID 1249569 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[CH:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][CH2:30][CH2:31][C:32](O)=[O:33])[CH:24]=1>CCCCCC>[F:22][C:19]1[CH:18]=[CH:17][C:16]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:9][CH:10]2[CH2:15][CH2:14][N:13]([C:32](=[O:33])[CH2:31][CH2:30][CH2:29][C:25]3[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=3)[CH2:12][CH2:11]2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 1143-Pyridinebutanoic acidHCID 137545034-[2,2-Bis(4-fluorophenyl)ethenyl]piperidine

Product 1

HCID 137545224-[2,2-Bis[4-fluorophenyl)ethenyl]1-[1-oxo-4-(3-pyridinyl)butyl]piperidineYield 65%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

The title compound was prepared in a manner similar to that employed for the compound of example 10 starting with 9.0 g of 4-[2,2-bis(4-fluorophenyl)ethenyl]piperidine, 0.15 molar hexane solvate and the acid chloride prepared from 6.6 g of 3-pyridine butanoic acid. The toluene extracts were evaporated and the residue was crystallized from ether to give 8.7 g (65%) of pure 4-[2,2-bis[4-fluorophenyl)ethenyl]1-[1-oxo-4-(3-pyridinyl)butyl]piperidine, mp 100°-102° C. Analysis Calculated for C28H28F2N2O: C, 75.31; H, 6.32; N, 6.27; F, 8.51. Found: C, 75.36; H, 6.30; N, 6.24; F, 8.30.

Workup

  1. customThe title compound was prepared in a manner similar to
  2. customThe toluene extracts were evaporated
  3. customthe residue was crystallized from ether

Sources & evidence

ORD record
ord-d60234eed3b7433684202935643f950f
Source dataset
uspto-grants-1986_12
Patent number
US04632925

Reaction notes

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