Water → HCID 19992280, compound

HRID 345487Notes

Reaction equation

HRID 345487 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.Cl[CH2:24][CH2:25][C:26]([N:28]([CH3:30])[CH3:29])=[O:27].C(=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O.[I-].[K+]>[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][C:26]([N:28]([CH3:30])[CH3:29])=[O:27])[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 32690663-chloro-N,N-dimethylpropanamideHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanol

Product 1

HCID 19992280HCID 19992280, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 10.0 g (0.033 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 4.5 g (0.033 mole) of 3-chloro-N,N-dimethylpropanamide, 14.0 g (0.132 mole) of anhydrous sodium carbonate and 0.3 g (0.002 mole) of potassium iodide in 100 ml of N,N-dimethylformamide was heated on a steam bath for 16 h. The mixture was poured into 2 L of water and extracted three times with 500 ml portions of ethyl acetate. The ethyl acetate fractions were combined, washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give a glass. Upon trituration with petroleum ether (30°-60° C.) the glass solidified to yield 13.2 g (100%) of a yellow solid. A portion of this solid was recrystallized from ethyl ether to give the title compound as a white solid, mp 134°-135° C.

Workup

  1. temperaturewas heated on a steam bath for 16 h
  2. extractionextracted three times with 500 ml portions of ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customto give a glass

Sources & evidence

ORD record
ord-4c0a2f555d09421e99c9f7174d63de9d
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Reaction notes

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