Potassium Iodide → HCID 86745168, compound

HRID 345495Notes

Reaction equation

HRID 345495 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:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[OH:9])=[CH:4][CH:3]=1.Br[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([N:31]([CH3:33])[CH3:32])=[O:30].[C:34](=[O:37])([O-:36])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C=O.O>[C:8]([OH:9])(=[O:30])[C:34]([OH:36])=[O:37].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)([OH:9])[CH:10]2[CH2:11][CH2:12][N:13]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([N:31]([CH3:33])[CH3:32])=[O:30])[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 10944045HCID 10944045, compoundHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanol

Product 1

HCID 86745168HCID 86745168, compoundYield 141%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.0 g (0.013 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 3.5 g (0.016 mole) of 6-bromo-N,N-dimethylhexanamide, 5.5 g (0.052 mole) of anhydrous sodium carbonate and 0.3 g (0.002 mole) of potassium iodide in 50 mL of N,N-dimethylformamide was stirred at ambient temperature for 16 h. The mixture was poured into 1 L of water and extracted twice with 250 mL of ethyl acetate. The combined ethyl acetate fractions were washed with water and brine, dried (MgSO4) and concentrated under reduced pressure. The residue was converted to the oxalic acid salt, and recrystallized from 2-propanol to yield 4.9 g (71%) of the title compound as a white solid, mp 157°-160° C.

Workup

  1. extractionextracted twice with 250 mL of ethyl acetate
  2. washThe combined ethyl acetate fractions were washed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-facb76b8e7424314a65cf62233a9762c
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Reaction notes

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