Hydroxylamine → HCID 86656732, compound

HRID 1257569Notes

Reaction equation

HRID 1257569 reaction equation
[CH2:1]([NH+:3]1[CH2:8][CH2:7][C:6](O)(O)[C:5]([F:12])([F:11])[CH2:4]1)[CH3:2].[NH2:13][OH:14]>C(O)C>[CH2:1]([N:3]1[CH2:8][CH2:7][C:6](=[N:13][OH:14])[C:5]([F:12])([F:11])[CH2:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 86656733HCID 86656733, compound

Product 1

HCID 86656732HCID 86656732, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A suspension of 1-ethyl-3,3-difluoro-4,4-dihydroxy-piperidinium (10.213 g, 46.93 mmol) in ethanol (80 ml) was charged with aqueous hydroxylamine solution (50% by weight, 3.58 ml, 58.4 mmol) and left to stand overnight. The thick precipitate was dissolved with the addition of ethanol (20 ml) and heating. The solution was then cooled to room temperature before being place over ice. The precipitated solid was then collected by filtration and dried over vacuum to yield 8.27 g 1-ethyl-3,3-difluoro-piperidin-4-one oxime (99%) LCMS (Method F): RT=0.14 min, m+H=179.0 1H NMR (400 MHz, D2O) δ 4.07-3.82 (m, 2H), 3.53 (s, 2H), 3.38 (q, J=7.3 Hz, 2H), 3.13 (s, 2H), 1.38 (t, J=7.3 Hz, 3H).

Workup

  1. waitleft
  2. temperatureheating
  3. filtrationThe precipitated solid was then collected by filtration
  4. customdried over vacuum

Sources & evidence

ORD record
ord-65c16ec5ac9a4fd0b579c11b9f58d2f4
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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