Hydrochloric Acid → HCID 70373424, compound

HRID 1709891Notes

Reaction equation

HRID 1709891 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.CCOCC.CC(O)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

8

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 2

HCID 6342AcetonitrileSolventHCID 22147583Diethyl ether 2-propanolSolvent

Procedure

A ixture of 3.0 g (0.01 mole) of [α,α-bis(p-fluorophenyl)]-4-piperidinemethanol, 3.1 g (0.01 mole) 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 ether/2-propanol 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. temperatureat reflux for 48 hr
  2. customgave a gum as residue
  3. customThe gum was purified by column chromatography on 120 g of Florisil®
  4. washThe desired fractions eluted with 10% acetone in benzene
  5. concentrationconcentrated under reduced pressure
  6. customto give a glass as residue
  7. customThe solid which precipitated
  8. filtrationwas collected by filtration
  9. customrecrystallized from absolute ethanol

Sources & evidence

ORD record
ord-cf08e2646f0849e38261c675b9032b42
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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