Water → 4-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinepropanamide

HRID 345475Notes

Reaction equation

HRID 345475 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]([NH2:28])=[O:27].C(=O)(O)[O-].[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]([NH2:28])=[O:27])[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 799823-Chloropropanimidic acidHCID 516892Sodium BicarbonateHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanol

Product 1

HCID 199923194-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinepropanamideYield 74.2%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 15.2 g (0.05 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 5.9 g (0.055 mole) of 3-chloropropionamide (Aldrich), 15.9 g (0.15 mole) of anhydrous sodium bicarbonate and 0.4 g of potassium iodide in 150 ml of dimethylformamide was heated on a steam bath for 24 h. The mixture was poured into 1.5 L of water and a solid precipitated. After standing overnight, the solid was collected by filtration, washed with water, dried, and recrystallized from benzene to yield 13.9 g (74%) of white solid, mp 136°-137° C.

Workup

  1. temperaturewas heated on a steam bath for 24 h
  2. customa solid precipitated
  3. filtrationthe solid was collected by filtration
  4. washwashed with water
  5. customdried
  6. customrecrystallized from benzene

Sources & evidence

ORD record
ord-c5271c6caa0c4ce393747d5908fb7381
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Reaction notes

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