Hydrochloric Acid → HCID 70373424, compound

HRID 1193707Notes

Reaction equation

HRID 1193707 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.[CH2:23]([O:25][C:26]([C:28]1[O:29][C:30]2[CH:38]=[C:37]([O:39][CH2:40][CH2:41][CH2:42][Cl:43])[CH:36]=[CH:35][C:31]=2[C:32](=[O:34])[CH:33]=1)=[O:27])[CH3:24].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].Cl>C(#N)C>[ClH:43].[CH2:23]([O:25][C:26]([C:28]1[O:29][C:30]2[CH:38]=[C:37]([O:39][CH2:40][CH2:41][CH2:42][N:13]3[CH2:12][CH2:11][CH:10]([C:8]([C:16]4[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=4)([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[OH:9])[CH2:15][CH2:14]3)[CH:36]=[CH:35][C:31]=2[C:32](=[O:34])[CH:33]=1)=[O:27])[CH3:24]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 9995573HCID 9995573, compoundHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanol

Product 1

HCID 70373424HCID 70373424, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3.0 g (0.01 mole) of [α,α-bis(p-fluorophenyl)]-4-piperidinemethanol, 3.1 g (0.01 mol) of 7-(3-chloropropoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid ethyl ester, 5.3 g (0.05 mole) of anhydrous sodium carbonate and 0.3 g of potassium iodide in 150 ml of acetonitrile heated at reflux for 48 hr gave a gum as residue. The gum was purified by column chromatography on 120 g of Florisil®. The desired fractions eluted with 10% acetone in benzene were combined and concentrated under reduced pressure to give a glass as residue. The glass was dissolved in etherisopropanol and treated with ethereal hydrogen chloride. The solid which precipitated was collected by filtration and recrystallized from absolute ethanol to give 1.9 g (31%) of white solid, m.p. 191° C. with decomposition.

Workup

  1. temperatureheated
  2. temperatureat reflux for 48 hr
  3. customgave a gum as residue
  4. customThe gum was purified by column chromatography on 120 g of Florisil®
  5. washThe desired fractions eluted with 10% acetone in benzene
  6. concentrationconcentrated under reduced pressure
  7. customto give a glass as residue
  8. dissolutionThe glass was dissolved in etherisopropanol
  9. customThe solid which precipitated
  10. filtrationwas collected by filtration
  11. customrecrystallized from absolute ethanol

Sources & evidence

ORD record
ord-14e65b61c163431996f9dd823dea80c2
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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