Potassium Iodide → alpha,alpha-Bis(4-fluorophenyl)-1-[3-(4-methylphenoxy)propyl]-4-piperidinemethanol fumarate

HRID 1709897Notes

Reaction equation

HRID 1709897 reaction equation
C(O)(=O)C(O)=O.C1(C(C2C=CC=CC=2)=C2CCN(CCCOC3C=CC=CC=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]([CH3:69])=[CH:65][CH:64]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].[C:78]([OH:85])(=[O:84])/[CH:79]=[CH:80]/[C:81]([OH:83])=[O:82]>C(O)CCC>[C:78]([OH:85])(=[O:84])/[CH:79]=[CH:80]/[C:81]([OH:83])=[O:82].[F:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]([C:51]2[CH:52]=[CH:53][C:54]([F:57])=[CH:55][CH:56]=2)([CH:45]2[CH2:46][CH2:47][N:48]([CH2:59][CH2:60][CH2:61][O:62][C:63]3[CH:64]=[CH:65][C:66]([CH3:69])=[CH:67][CH:68]=3)[CH2:49][CH2:50]2)[OH:44])=[CH:39][CH:38]=1

Participants

8

Reactant 6

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 444972Fumaric AcidHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 126856111-(3-Chloropropoxy)-4-methylbenzeneHCID 230363354-(Diphenylmethylene)-1-(3-phenoxypropyl)piperidine oxalate

Product 1

HCID 23036310alpha,alpha-Bis(4-fluorophenyl)-1-[3-(4-methylphenoxy)propyl]-4-piperidinemethanol fumarateYield 56%

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, 1.8 g (0.01 mole) of 1-chloro-3-(4-methylphenoxy) 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 gum as residue. The gum was purified by column chromatography on 100 g of Florisil®. Fractions eluted with 10% acetone in benzene were combined and concentrated to give a gum. This gum was converted to the fumaric acid salt and the solid was recrystallized from absolute ethanol to yield 3.2 g (56%) of title compound as a white solid, mp 193°-194° C. with decomposition. pe f 49495948.hsc

Workup

  1. customThis compound was prepared
  2. customgave a gum as residue
  3. customThe gum was purified by column chromatography on 100 g of Florisil®
  4. washFractions eluted with 10% acetone in benzene
  5. concentrationconcentrated
  6. customto give a gum
  7. customthe solid was recrystallized from absolute ethanol

Sources & evidence

ORD record
ord-24ade4ff58564bfd9d5cfa14ac7b0472
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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