Potassium Carbonate → HCID 69423625, compound

HRID 1350124Notes

Reaction equation

HRID 1350124 reaction equation
CC1(O)C(=[N:8][CH:9]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH2:10][CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)CC2CC1C2(C)C.Cl.NO.C([O-])([O-])=O.[K+].[K+]>C(O)C>[N:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C@H:9]([NH2:8])[CH2:10][CH2:11][CH:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 21094262HCID 21094262, compound

Product 1

HCID 69423625HCID 69423625, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,6,6-trimethyl-3-(1-(3-pyridyl)-3-(4-oxanyl)propylimino]bicyclo[3.1.1]heptan-2-ol (1.85 g, 5.0 mmol) in ethanol (20 mL) was added hydroxylamine hydrochloride (2.00 g, 28.8 mmol) and K2CO3 (3.98 g, 28.8 mmol) and the mixture was heated to reflux for 16 h. The reaction was then cooled to room temperature, filtered through Celite, washed with ethanol, concentrated by rotary evaporation and purified by column chromatography, using a gradient of chloroform:methanol:ammonium hydroxide (90:9:1 to 80:19:1) eluent, to yield 0.88 g of a light yellow oil (80% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 16 h
  3. filtrationfiltered through Celite
  4. washwashed with ethanol
  5. concentrationconcentrated by rotary evaporation
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-4ccd22a9fea24132a94130b1a541323e
Source dataset
uspto-grants-2007_05
Patent number
US07214686B2

Reaction notes

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