Trifluoroacetic acid → 4-[2,2-Bis(4-fluorophenyl)ethenyl]piperidine

HRID 1249566Notes

Reaction equation

HRID 1249566 reaction equation
C1(C(C2C=CC=CC=2)=CC2CCNCC2)C=CC=CC=1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([C:37]2[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=2)(O)[CH2:29][CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:24][CH:23]=1.FC(F)(F)C(O)=O>CC1C=CC=CC=1>[F:43][C:40]1[CH:41]=[CH:42][C:37]([C:28]([C:25]2[CH:24]=[CH:23][C:22]([F:21])=[CH:27][CH:26]=2)=[CH:29][CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 13754500HCID 13754500, compoundHCID 13754513alpha,alpha-Bis(4-fluorophenyl)-4-piperidineethanol

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared in the same manner as the compound of example 6, starting with 25 g of alpha,alpha-bis(4-fluorophenyl)-4-piperidineethanol, 0.25 molar methylbenzene solvate and 50 mL of trifluoroacetic acid. Crystallization from hexane gave 19.6 g (83%) of the hexane solvate of 4-[2,2-bis(4-fluorophenyl)ethenyl]-piperidine, mp 84°-86° C. Analysis Calculated for C19H19F2N.O.15C6H14 : C, 76.54; H, 6.81; N, 4.49; F, 12.17. Found: C, 76.87; H, 6.72; 4.65; F, 12.12.

Workup

  1. customCrystallization from hexane

Sources & evidence

ORD record
ord-95bdbf6fb7a0479f88cdd5c073c7d8a2
Source dataset
uspto-grants-1986_12
Patent number
US04632925

Reaction notes

Loading…