1,1'-(4-Chlorobutylidene)bis(4-fluorobenzene) → 1-[4,4-Bis-(4-fluorophenyl)butyl]-4-(2,3,4,5,6-pentafluorophenoxy)piperidine

HRID 1031543Notes

Reaction equation

HRID 1031543 reaction equation
C(=O)(O)[O-].[Na+].[F:6][C:7]1[C:19]([F:20])=[C:18]([F:21])[C:17]([F:22])=[C:16]([F:23])[C:8]=1[O:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[F:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)[CH2:32][CH2:33][CH2:34]Cl)=[CH:27][CH:26]=1>CN(C)C=O>[F:24][C:25]1[CH:26]=[CH:27][C:28]([CH:31]([C:36]2[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=2)[CH2:32][CH2:33][CH2:34][N:13]2[CH2:14][CH2:15][CH:10]([O:9][C:8]3[C:16]([F:23])=[C:17]([F:22])[C:18]([F:21])=[C:19]([F:20])[C:7]=3[F:6])[CH2:11][CH2:12]2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 516892Sodium BicarbonateHCID 148370404-(2,3,4,5,6-Pentafluorophenoxy)piperidine

Product 1

HCID 148370581-[4,4-Bis-(4-fluorophenyl)butyl]-4-(2,3,4,5,6-pentafluorophenoxy)piperidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
78 °C

Procedure

A stirring mixture of 10 g of sodium bicarbonate in 50 ml dimethylformamide was treated with 4.0 g of 4-(2,3,4,5,6-pentafluorophenoxy)piperidine followed by a solution of 4.06 ml of 4,4-bis-(4-fluorophenyl)butyl chloride in 10 ml of dimethylformamide, and then stirred at 78° C. for 20 hours. After filtering, the filtrate was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. Filtration followed by evaporation of the volatiles afforded a residue which was purified by means of high pressure liquid chromatography (silica gel; elution with 20% ethyl acetate/dichloromethane) to afford 5.44 g of 1-[4,4-bis-(4-fluorophenyl)butyl]-4-(2,3,4,5,6-pentafluorophenoxy)piperidine as an oil. The oil was dissolved in hot isopropanol and acidified with an etheral solution of oxalic acid to precipitate the corresponding oxalate salt. Recrystallization from isopropanol afforded 2.75 g (30.0%) of 1-[4,4-bis-(4-fluorophenyl)butyl]-4-(2,3,4,5,6-pentafluorophenoxy)piperidine oxalate, m.p. 183°-185° C.

Workup

  1. filtrationAfter filtering
  2. additionthe filtrate was poured into water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationFiltration
  7. customfollowed by evaporation of the volatiles
  8. customafforded a residue which
  9. customwas purified by means of high pressure liquid chromatography (silica gel; elution with 20% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-5b8013dd2e9d497ba06dac0324966d97
Source dataset
uspto-grants-1990_09
Patent number
US04954511

Reaction notes

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