Potassium Iodide → 1-[3-(4-Fluorophenoxy)propyl]-alpha,alpha-bis(4-fluorophenyl)-4-piperidinemethanol fumarate hydrate

HRID 1709898Notes

Reaction equation

HRID 1709898 reaction equation
C(O)(=O)C(O)=[O:3].C1(C(C2C=CC=CC=2)=C2CCN(CCC[O:23][C:24]3C=CC=[CH:26][CH:25]=3)CC2)C=CC=CC=1.[F:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]([C:51]2[CH:56]=[CH:55][C:54]([F:57])=[CH:53][CH:52]=2)([CH:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)[OH:44])=[CH:39][CH:38]=1.Cl[CH2:59][CH2:60][CH2:61][O:62][C:63]1[CH:68]=[CH:67][C:66]([F:69])=[CH:65][CH:64]=1.[C:70](=[O:73])([O-:72])[O-].[Na+].[Na+].[I-].[K+]>C(O)CCC>[OH2:3].[C:24]([OH:44])(=[O:23])/[CH:25]=[CH:26]/[C:70]([OH:72])=[O:73].[F:69][C:66]1[CH:67]=[CH:68][C:63]([O:62][CH2:61][CH2:60][CH2:59][N:48]2[CH2:47][CH2:46][CH:45]([C:43]([C:51]3[CH:52]=[CH:53][C:54]([F:57])=[CH:55][CH:56]=3)([C:40]3[CH:41]=[CH:42][C:37]([F:36])=[CH:38][CH:39]=3)[OH:44])[CH2:50][CH2:49]2)=[CH:64][CH:65]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 743911-(3-Chloropropoxy)-4-fluorobenzeneHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 230363354-(Diphenylmethylene)-1-(3-phenoxypropyl)piperidine oxalate

Product 1

HCID 230362891-[3-(4-Fluorophenoxy)propyl]-alpha,alpha-bis(4-fluorophenyl)-4-piperidinemethanol fumarate hydrateYield 39%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

This compound was prepared according to the procedure used to synthesize the compound of Example 1. A mixture of 3.0 g (0.01 mole) of α,α-bis (p-fluorophenyl)-4-piperidinemethanol, 1.9 g (0.01 mole) of 1-chloro-3-(4-fluorophenoxy) propane, 5.3 g (0.035 mole) of anhydrous sodium carbonate and 0.3 g of potassium iodide in 100 ml of 1-butanol gave a solid as residue. The solid was further purified by column chromatography on 60 g of Florisil®. Fractions eluted with 2-10% acetone in benzene were combined and concentrated to give a solid residue. The solid was converted to the furmaric acid salt and this solid was recrystallized from isopropanol to yield 2.2 g (39%) of title compound as a white solid, mp 155°-157° C.

Workup

  1. customThis compound was prepared
  2. customgave a solid as residue
  3. customThe solid was further purified by column chromatography on 60 g of Florisil®
  4. washFractions eluted with 2-10% acetone in benzene
  5. concentrationconcentrated
  6. customto give a solid residue
  7. customthis solid was recrystallized from isopropanol

Sources & evidence

ORD record
ord-7ae97e7b12c543a1b7cafb8f59ebde5d
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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