Water → HCID 86745162, compound

HRID 345474Notes

Reaction equation

HRID 345474 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.[C:23](=[O:26])([O-])[O-].[Na+].[Na+].O.[CH3:30][N:31](C)[CH:32]=[O:33]>[I-].[K+]>[CH2:2]([O:26][CH2:23][CH3:30])[CH3:3].[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]([CH2:23][C:32]([NH2:31])=[O:33])[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanol

Product 1

HCID 86745162HCID 86745162, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 4875Potassium IodideCatalyst

Procedure

A mixture of 15.2 g (0.05 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol (U.S. Pat. No. 3,956,296), 5.1 g (0.055 mole) of 1-chloroacetamide, 15.9 g (0.15 mole) of anhydrous sodium carbonate and 0.4 g of potassium iodide in 150 ml of dimethylformamide was heated on a steam bath for 22 h. The mixture was poured into 1.5 L of water and a gum precipitated which crystallized upon standing overnight. The solid was collected by filtration, washed with water, dried, and recrystallized from 2-propanol/petroleum ether (30°-60° C.) to yield 11.7 g (65%) of the amide as an off-white solid. An analytical sample, mp 117°-119° C. (dec), was prepared from benzene-ethyl ether.

Workup

  1. customa gum precipitated which
  2. customcrystallized
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. customdried
  6. customrecrystallized from 2-propanol/petroleum ether (30°-60° C.)

Sources & evidence

ORD record
ord-3c1ffaa67696417da8ddb1ec5366f817
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Reaction notes

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