Potassium Iodide → HCID 23036407, compound

HRID 1709910Notes

Reaction equation

HRID 1709910 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:58][CH:59]([CH2:75][CH3:76])[CH2:60][CH2:61][CH2:62][O:63][C:64]1[CH:69]=[CH:68][C:67]([C:70](=[O:72])[CH3:71])=[CH:66][C:65]=1[O:73][CH3:74].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(O)CCC.C(OCC)C>[ClH:58].[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)([OH:44])[CH:45]2[CH2:46][CH2:47][N:48]([CH2:76][CH2:75][CH2:59][CH2:60][CH2:61][CH2:62][O:63][C:64]3[CH:69]=[CH:68][C:67]([C:70](=[O:72])[CH3:71])=[CH:66][C:65]=3[O:73][CH3:74])[CH2:49][CH2:50]2)=[CH:39][CH:38]=1

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 23036325HCID 23036325, compoundHCID 230363354-(Diphenylmethylene)-1-(3-phenoxypropyl)piperidine oxalate

Product 1

HCID 23036407HCID 23036407, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 3283Diethyl EtherSolvent

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, 2.8 g (0.01 mole) of 1-[4-(4-chlorohexyloxy)-3-methoxyphenyl]ethanone, 5.3 g (0.05 mole) of anhydrous sodium carbonate and 0.3 g of potassium iodide in 100 ml of 1-butanol gave a gum as resiude. The gum was purified by column chromatography on 80 g of Florisil®. Fractions eluted with 2-5% acetone in benzene were combined and concentrated to give a glass as residue. The glass was dissolved in anhydrous ethyl ether, filtered and the filtrate treated with ethereal hydrogen chloride. A gummy solid precipitated. This solid was triturated with fresh ethyl ether until a fine, white solid resulted. The solid was collected by filtration and dried to yield 1.0 g (17%) of title compound as a white solid, mp 182°-186° C. with decomposition.

Workup

  1. customThis compound was prepared
  2. customgave a gum as resiude
  3. customThe gum was purified by column chromatography on 80 g of Florisil®
  4. washFractions eluted with 2-5% acetone in benzene
  5. concentrationconcentrated
  6. customto give a glass as residue
  7. filtrationfiltered
  8. additionthe filtrate treated with ethereal hydrogen chloride
  9. customA gummy solid precipitated
  10. customThis solid was triturated with fresh ethyl ether until a fine, white solid
  11. customresulted
  12. filtrationThe solid was collected by filtration
  13. customdried

Sources & evidence

ORD record
ord-512bcf8cef3b4ad7b0d0a02d3ca030e4
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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