Sodium Carbonate → HCID 15042239, compound

HRID 973414Notes

Reaction equation

HRID 973414 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][OH:27].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.[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][CH2:26][OH:27])[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 123083-Bromo-1-propanolHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanol

Product 1

HCID 15042239HCID 15042239, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 30.3 g (0.10 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 16.1 g (0.11 mole) of 3-bromo-1-propanol (95% purity, Aldrich), 37.1 g (0.35 mole) of anhydrous sodium carbonate and 1.0 g of potassium iodide in 300 ml of DMF was heated on a steam bath for 20 h. The mixture was converted and the residue partitioned between water and benzene. The benzene layer was washed with water and brine, dried (sodium sulfate) and concentrated to give a gummy solid. The solid was recrystallized from 2-propanol/isopropyl ether to yield 23.3 g (65%) of a white solid, mp 155°-157° C.

Workup

  1. temperaturewas heated on a steam bath for 20 h
  2. customthe residue partitioned between water and benzene
  3. washThe benzene layer was washed with water and brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated
  6. customto give a gummy solid
  7. customThe solid was recrystallized from 2-propanol/isopropyl ether

Sources & evidence

ORD record
ord-3df3996092e04e4bbbd311677f939aa9
Source dataset
uspto-grants-1991_11
Patent number
US05063235

Reaction notes

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