Potassium Iodide → HCID 86744176, compound

HRID 1709935Notes

Reaction equation

HRID 1709935 reaction equation
C(O)(=O)C(O)=O.C1(C(C2C=CC=CC=2)=C2CCN(CCCOC3C=CC=CC=3)CC2)C=CC=CC=1.Cl.[F:37][C:38]1[CH:43]=[CH:42][C:41]([C:44]([C:53]2[CH:58]=[CH:57][C:56]([F:59])=[CH:55][CH:54]=2)([OH:52])[CH2:45][CH:46]2[CH2:51][CH2:50][CH2:49][NH:48][CH2:47]2)=[CH:40][CH:39]=1.Cl[CH2:61][CH2:62][CH2:63][O:64][C:65]1[CH:70]=[CH:69][C:68]([C:71](=[O:73])[CH3:72])=[CH:67][C:66]=1[O:74][CH3:75].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].[C:84]([OH:91])(=[O:90])/[CH:85]=[CH:86]/[C:87]([OH:89])=[O:88]>C(O)CCC>[C:84]([OH:91])(=[O:90])/[CH:85]=[CH:86]/[C:87]([OH:89])=[O:88].[F:37][C:38]1[CH:43]=[CH:42][C:41]([C:44]([C:53]2[CH:54]=[CH:55][C:56]([F:59])=[CH:57][CH:58]=2)([OH:52])[CH2:45][CH:46]2[CH2:51][CH2:50][CH2:49][N:48]([CH2:61][CH2:62][CH2:63][O:64][C:65]3[CH:70]=[CH:69][C:68]([C:71](=[O:73])[CH3:72])=[CH:67][C:66]=3[O:74][CH3:75])[CH2:47]2)=[CH:40][CH:39]=1

Participants

8

Reactant 6

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 444972Fumaric AcidHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenoneHCID 230363354-(Diphenylmethylene)-1-(3-phenoxypropyl)piperidine oxalateHCID 70373355HCID 70373355, compound

Product 1

HCID 86744176HCID 86744176, compoundYield 35%

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 3.7 g (0.012 mole) of the base of [α,α-bis(4-fluoropheny]-3-piperidineethanol hydrochloride [1:1], 2.8 g free (0.012 mole) of 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone, 4.3 g (0.04 mole) of anhydrous sodium carbonate and 0.5 g of potassium iodide in 100 ml of 1-butanol gave a gum as residue. The gum was purified by column chromatography on 120 g of Florisil®. Fractions eluted with 20-60% 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 ethyl acetate-acetonitrile to yield 2.6 g (35%) of the title compound as a white solid, mp 133°-136° C.

Workup

  1. customThis compound was prepared
  2. customgave a gum as residue
  3. customThe gum was purified by column chromatography on 120 g of Florisil®
  4. washFractions eluted with 20-60% acetone in benzene
  5. concentrationconcentrated
  6. customto give a gum
  7. customthe solid was recrystallized from ethyl acetate-acetonitrile

Sources & evidence

ORD record
ord-b4dabe5cf3444b29a8f7120e145f1ba1
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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