Water → HCID 54390795, compound

HRID 345493Notes

Reaction equation

HRID 345493 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][C:25]([NH:27][CH3:28])=[O:26].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][C:25]([NH:27][CH3:28])=[O:26])[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 667732-chloro-N-methylacetamideHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanol

Product 1

HCID 54390795HCID 54390795, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 12.1 g (0.040 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 5.2 g (0.048 mole) of 2-chloro-N-methylacetamide, 17.0 g (0.160 mole) of anhydrous sodium carbonate and 0.4 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 1.5 L of water and extracted twice with 500 mL portions of ethyl acetate. The ethyl acetate layers were combined, washed with water and brine, dried (MgSO4), and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to yield 14.2 g (95%) of white solid, mp 122°-124° C.

Workup

  1. temperaturewas heated on a steam bath for 16 h
  2. extractionextracted twice with 500 mL portions of ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a8a4b5f64ad94e938c1e071782d66b0a
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Reaction notes

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