Pyridine → HCID 10103749, compound

HRID 550883Notes

Reaction equation

HRID 550883 reaction equation
[O:1]([NH2:3])[CH3:2].N1C=CC=CC=1.[CH:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[C:11]1=O)[CH2:17]2>Cl.CO>[CH3:2][O:1][N:3]=[C:11]1[CH:12]2[CH2:18][CH:16]3[CH2:15][CH:14]([CH2:19][CH:10]1[CH2:17]3)[CH2:13]2

Participants

6

Reactant 3

HCID 1049PyridineHCID 4113O-MethylhydroxylamineHCID 64151Adamantanone

Product 1

HCID 10103749HCID 10103749, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

3.76 g (45 mmol) of methoxylamine, in hydrochloride form, and 4.36 g (55.1 mmol) of pyridine are added to 4.51 g (30 mmol) of 2-adamantanone in 30 ml of methanol. The reaction medium is stirred at ambient temperature for 66 h, the solvents are evaporated off under vacuum, and the residue is then diluted with 50 ml of dichloromethane and 50 ml of water. The organic phase is separated and the aqueous phase is then extracted again with 30 ml of dichloromethane. The organic phases are combined, washed with two times 30 ml of dilute hydrochloric acid (1 M) and 30 ml of brine, and then dried over magnesium sulphate. After filtration and evaporation in a rotary evaporator, the product 35 is obtained in the form of a white powder: 3.57 g (yield=66%).

Workup

  1. customthe solvents are evaporated off under vacuum
  2. additionthe residue is then diluted with 50 ml of dichloromethane and 50 ml of water
  3. customThe organic phase is separated
  4. extractionthe aqueous phase is then extracted again with 30 ml of dichloromethane
  5. washwashed with two times 30 ml of dilute hydrochloric acid (1 M) and 30 ml of brine
  6. dry with materialdried over magnesium sulphate
  7. filtrationAfter filtration and evaporation
  8. customin a rotary evaporator

Sources & evidence

ORD record
ord-95d5ba09d5374abe991db6b42fb15e5f
Source dataset
uspto-grants-2011_05
Patent number
US07947701B2

Reaction notes

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