Potassium Iodide → 4-[Bis(4-fluorophenyl)hydroxymethyl]-N-phenyl-1-piperidinepropanamide

HRID 345476

Reaction equation

HRID 345476 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]([NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C=O.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][C:26]([NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:27])[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 2404043-chloro-N-phenylpropanamideHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanol

Product 1

HCID 199922514-[Bis(4-fluorophenyl)hydroxymethyl]-N-phenyl-1-piperidinepropanamideYield 60.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.0 g (0.007 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 2.6 g (0.014 mole) of 3-chloro-N-phenylpropanamide, 8.5 g (0.080 mole) of anhydrous sodium carbonate and 0.3 g (0.002 mole) of potassium iodide in 50 ml of N,N-dimethylformamide was heated on a steam bath for 16 hours. The mixture was poured into 500 ml of water and extracted twice with 250 ml portions of ethyl acetate. The combined extracts were washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give an off-white solid. The solid was recrystallized from methanol/2-propanol to yield 1.9 g (59%) of white solid, mp 190°-192° C.

Workup

  1. temperaturewas heated on a steam bath for 16 hours
  2. extractionextracted twice with 250 ml portions of ethyl acetate
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customto give an off-white solid
  7. customThe solid was recrystallized from methanol/2-propanol

Sources & evidence

ORD record
ord-b33e3e23225a46b285543c1fa7cb5240
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Linked notes

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