N-Ethylhydroxylamine hydrochloride → 2-(6,11-dihydrodibenz[b,e]oxepin-2-yl)-N-ethyl-N-hydroxyethylamine

HRID 1417097Notes

Reaction equation

HRID 1417097 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:22]=[CH:21][C:11]2[O:12][CH2:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[CH2:16][C:10]=2[CH:9]=1)(=O)=O.Cl.[CH2:24]([NH:26]O)[CH3:25].CC(C)([O-:31])C.[K+]>C(O)C>[CH:9]1[C:10]2[CH2:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[CH2:13][O:12][C:11]=2[CH:21]=[CH:22][C:8]=1[CH:7]([OH:31])[CH2:6][NH:26][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 10219386N-Ethylhydroxylamine hydrochlorideHCID 107106752-(6,11-Dihydrodibenz[b,e]oxepin-2-yl)ethanol methanesulfonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 867533642-(6,11-dihydrodibenz[b,e]oxepin-2-yl)-N-ethyl-N-hydroxyethylamineYield 14.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-(6,11-Dihydrodibenz[b,e]oxepin-2-yl)ethanol methanesulfonate (13.5 g) was taken up in 20 ml of absolute ethanol and added to a solution containing ethyl hydroxylamine hydrochloride (11.03 g) and potassium t-butoxide (12.7 g) in 600 ml of absolute ethanol. The mixture was stirred at reflux under a nitrogen blanket for 18 hours then evaporated. The residue was taken up in chloroform and washed with brine, dried, and evaporated. Purification of the residual oil (HPLC, 9:1 DCM-methanol) gave an oil which crystallized from ether-hexane. Recrystallization from ether-cyclohexane gave 1.7 g of 2-(6,11-dihydrodibenz[b,e]oxepin-2-yl)-N-ethyl-N-hydroxyethylamine, as crystals, m.p 102-103° C., with softening at 88° C.

Workup

  1. additionadded to a solution
  2. temperatureat reflux under a nitrogen blanket for 18 hours
  3. customthen evaporated
  4. washwashed with brine
  5. customdried
  6. customevaporated
  7. customPurification of the residual oil (HPLC, 9:1 DCM-methanol)
  8. customgave an oil which
  9. customcrystallized from ether-hexane
  10. customRecrystallization from ether-cyclohexane

Sources & evidence

ORD record
ord-f58076e676404ba1b9feea0884e85725
Source dataset
uspto-grants-1999_06
Patent number
US05917057

Reaction notes

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