Potassium Iodide → HCID 23036294, compound

HRID 1193684Notes

Reaction equation

HRID 1193684 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:23][CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35](=[O:37])[CH3:36])=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(O)CCC.C(OCC)C>[OH2:9].[ClH:23].[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][CH2:26][O:27][C:28]3[CH:33]=[CH:32][C:31]([NH:34][C:35](=[O:37])[CH3:36])=[CH:30][CH:29]=3)[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 5147668N-[4-(3-chloropropoxy)phenyl]acetamideHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanol

Product 1

HCID 23036294HCID 23036294, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3.0 g (0.01 mole) of [α,α-bis(p-fluorophenyl)]-4-piperidinemethanol, 2.3 g (0.01 mole) of N-[4-(3-chloropropoxy)phenyl]acetamide, 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 residue. The gum was purified by column chromatography on 80 g of Florisil® and the product was eluted with 20% acetone in benzene. The combined fractions containing product were concentrated under reduced pressure to give a glass as residue. The glass was dissolved in ethyl ether, filtered through cotton, and the filtrate treated with ethereal hydrogen chloride. The resulting solid was collected by filtration, washed with ethyl ether and dried to yield 2.1 g (38%) of white solid, m.p. 135°-170° C. (with decomposition).

Workup

  1. customgave a gum as residue
  2. customThe gum was purified by column chromatography on 80 g of Florisil®
  3. washthe product was eluted with 20% acetone in benzene
  4. additionThe combined fractions containing product
  5. concentrationwere concentrated under reduced pressure
  6. customto give a glass as residue
  7. filtrationfiltered through cotton
  8. additionthe filtrate treated with ethereal hydrogen chloride
  9. filtrationThe resulting solid was collected by filtration
  10. washwashed with ethyl ether
  11. customdried

Sources & evidence

ORD record
ord-50a0a894521f4a888937cc0a0a534734
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

Loading…