O-(prop-2-yn-1-yl)hydroxylamine hydrochloride → HCID 86744767, compound

HRID 2050892Notes

Reaction equation

HRID 2050892 reaction equation
Cl.[C:2]([CH:5]1[CH:10]2[CH2:11][CH2:12][N:7]([CH2:8][CH2:9]2)[CH2:6]1)(=O)[CH3:3].Cl.[CH2:14]([O:17][NH2:18])[C:15]#[CH:16]>CO>[CH2:14]([O:17][N:18]=[C:2]([CH:5]1[CH:10]2[CH2:11][CH2:12][N:7]([CH2:8][CH2:9]2)[CH2:6]1)[CH3:3])[C:15]#[CH:16]

Participants

4

Reactant 2

HCID 13502403O-(prop-2-yn-1-yl)hydroxylamine hydrochlorideHCID 197994593-Acetyl quinuclidine hydrochloride

Product 1

HCID 86744767HCID 86744767, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.8 g of 3-acetyl quinuclidine hydrochloride and 1.02 g of O-2-propynyl-hydroxylamine hydrochloride are heated for 20 minutes to reflux in 30 cm3 of methanol. After evaporating to dryness, the residue is chromatographed on silica (eluant: methanol-ethyl ether). An aqueous solution of potassium carbonate is added and extraction is carried out with ethyl acetate. The extracts are dried and distilled at 170° C. under 0.2 mbar. After cooling, 1.1 g of expected product is obtained. M.p.=56°-58° C.

Workup

  1. customAfter evaporating to dryness
  2. customthe residue is chromatographed on silica (eluant: methanol-ethyl ether)
  3. additionAn aqueous solution of potassium carbonate is added
  4. extractionextraction
  5. customThe extracts are dried
  6. distillationdistilled at 170° C. under 0.2 mbar
  7. temperatureAfter cooling

Sources & evidence

ORD record
ord-740dc543f1904e88800b229b5c614a5d
Source dataset
uspto-grants-1991_05
Patent number
US05015655

Reaction notes

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