N-methylhydroxylamine hydrochloride → HCID 10827845, compound

HRID 357254Notes

Reaction equation

HRID 357254 reaction equation
Cl.[CH3:2][NH:3][OH:4].CC(C)([O-])C.[K+].CS(O[CH2:16][CH2:17][CH2:18][C:19]1[CH:34]=[CH:33][C:22]2[O:23][CH2:24][C:25]3[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=3[C:27](=[O:28])[C:21]=2[CH:20]=1)(=O)=O>C(O)C>[O:28]=[C:27]1[C:26]2[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=2[CH2:24][O:23][C:22]2[CH:33]=[CH:34][C:19]([CH2:18][CH2:17][CH2:16][N:3]([OH:4])[CH3:2])=[CH:20][C:21]1=2

Participants

5

Reactant 3

HCID 77906N-methylhydroxylamine hydrochlorideHCID 23665647Potassium tert-butoxideHCID 88429698HCID 88429698, compound

Product 1

HCID 10827845HCID 10827845, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring solution of 13.06 g of N-methylhydroxylamine hydrochloride in 250 ml of absolute ethanol was added 17.48 g of potassium tert-butoxide. To the resulting suspension was added 9.0 g of 3-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)propanol methanesulfonate. The resulting product suspension was allowed to reflux for 24 hours and was then cooled to room temperature. The suspension was filtered to remove potassium chloride, and the mother liquor was then treated with 200 ml of water and concentrated in vacuo to remove ethanol. The resulting mixture was partitioned against a total of 450 ml of methylene chloride and 250 ml of water. The organic phase was washed with 250 ml of saturated sodium chloride solution, dried (Na2SO4), filtered, and concentrated in vacuo to a viscous oil which solidified upon triturating the oil, with 10 ml of ethyl acetate and 3 drops of hexane and refrigerating. Thin layer analysis of the solids indicated a mixture, which was separated via HPLC (silica gel). The purified oil solidified upon standing to give 4.03 g of 3-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)-N-hydroxy-N-methyl-1-propylamine m.p. 113°-114.5° C.

Workup

  1. temperatureto reflux for 24 hours
  2. filtrationThe suspension was filtered
  3. customto remove potassium chloride
  4. additionthe mother liquor was then treated with 200 ml of water
  5. concentrationconcentrated in vacuo
  6. customto remove ethanol
  7. customThe resulting mixture was partitioned against a total of 450 ml of methylene chloride and 250 ml of water
  8. washThe organic phase was washed with 250 ml of saturated sodium chloride solution
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo to a viscous oil which
  12. customupon triturating the oil
  13. customwas separated via HPLC (silica gel)

Sources & evidence

ORD record
ord-340f6ab25d034976a9c3a233dc30e189
Source dataset
uspto-grants-1998_11
Patent number
US05840749

Reaction notes

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