Potassium Iodide → 4-[Bis(4-fluorophenyl)hydroxymethyl]-N-methyl-1-piperidinepentanamide

HRID 345494Notes

Reaction equation

HRID 345494 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][CH2:26][CH2:27][C:28]([NH:30][CH3:31])=[O:29].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C=O.C(OCC)C.O>[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][C:28]([NH:30][CH3:31])=[O:29])[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 199923245-Chloro-N-methylpentanamide

Product 1

HCID 199922774-[Bis(4-fluorophenyl)hydroxymethyl]-N-methyl-1-piperidinepentanamideYield 71%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 6.1 g (0.020 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 3.7 g (0.025 mole) of 5-chloro-N-methylpentanamide, 8.5 g (0.080 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 24 h. The mixture was poured into 1.5 L of water and extracted twice with 500 ml portions of ethyl acetate. The ethyl acetate portions were combined, washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give a golden oil. The oil was dissolved in ethyl ether and allowed to stand, whereupon a white solid precipitated. The solid was collected by filtration, and recrystallized from ethyl ether to yield 5.9 g (71%) of white solid, mp 130°-131° C.

Workup

  1. extractionextracted twice with 500 ml portions of ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customto give a golden oil
  6. customprecipitated
  7. filtrationThe solid was collected by filtration
  8. customrecrystallized from ethyl ether

Sources & evidence

ORD record
ord-f56639b255ec472db262e155f4c14e76
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Reaction notes

Loading…