Pyridine → HCID 86752826, compound

HRID 1377743Notes

Reaction equation

HRID 1377743 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=O)[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[ClH:27].Cl.[NH2:29][CH2:30][CH2:31][O:32][NH2:33].N1C=CC=CC=1>C(O)C>[ClH:27].[ClH:27].[NH2:29][CH2:30][CH2:31][O:32][N:33]=[C:17]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:16][CH2:15][CH2:14][N:11]1[CH2:12][CH2:13][CH:8]([C:6](=[O:7])[C:5]2[CH:25]=[CH:26][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10066660HCID 10066660, compoundHCID 143623262-(O-aminooxy)ethylamine dihydrochloride

Product 1

HCID 86752826HCID 86752826, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-[4-(4-fluorobenzoyl)-1-piperdinyl]-1-phenyl-1-butanone (5.00 g), O-(2-aminoethyl)hydroxylamine dihydrochloride (2.21 g), 3 equivalents of pyridine, and absolute ethanol (75 ml) was stirred at 60° C., overnight, under nitrogen. The reaction mixture was evaporated, toluene was added and evaporated. The reaction mixture was partitioned between 10% sodium hydroxide solution and ethyl acetate. The layers were separated and the aqueous phase extracted with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated. The residue was purified by flash chromatography (180:19:1 dichloromethane/methanol/ammonium hydroxide). The appropriate fractions were collected and evaporated. The residue was dissolved in absolute ethanol and treated with ethereal hydrogen chloride. Diethyl ether was added. The precipitate was collected and recrystallized twice from absolute ethanol/ether to give 2.3 g (34%) of product, mp 110°-115° C. (dec).

Workup

  1. customThe reaction mixture was evaporated
  2. additiontoluene was added
  3. customevaporated
  4. customThe reaction mixture was partitioned between 10% sodium hydroxide solution and ethyl acetate
  5. customThe layers were separated
  6. extractionthe aqueous phase extracted with ethyl acetate
  7. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customthe filtrate was evaporated
  10. customThe residue was purified by flash chromatography (180:19:1 dichloromethane/methanol/ammonium hydroxide)
  11. customThe appropriate fractions were collected
  12. customevaporated
  13. dissolutionThe residue was dissolved in absolute ethanol
  14. additiontreated with ethereal hydrogen chloride
  15. additionDiethyl ether was added
  16. customThe precipitate was collected
  17. customrecrystallized twice from absolute ethanol/ether

Sources & evidence

ORD record
ord-0ee5552ea78e4404b9247c0928c06bb3
Source dataset
uspto-grants-1997_09
Patent number
US05665756

Reaction notes

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