Potassium Hydroxide → HCID 22278881, compound

HRID 1063326Notes

Reaction equation

HRID 1063326 reaction equation
[OH-].[K+].Cl.CN.[C:6]([N:11]1[CH2:16][CH:15]([CH3:17])[C:14](=O)[CH:13]([CH3:19])[CH2:12]1)([O:8][CH2:9][CH3:10])=[O:7].[C:20]([BH3-])#[N:21].[Na+]>CO>[CH3:20][NH:21][CH:14]1[CH:15]([CH3:17])[CH2:16][N:11]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:12][CH:13]1[CH3:19]

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 222788871-Carbethoxy-3,5-dimethyl-4-piperidinone

Product 1

HCID 22278881HCID 22278881, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
10 °C

Procedure

Powdered KOH (0.92 g, 16.44 mmol) was added in portions to the stirred solution of methylamine hydrochloride (1.11 g, 16.44 mmol) in methanol (20 ml) at 0-5° C. and 1-carbethoxy-3,5-dimethyl-4-piperidinone (2.2 g, 1.1 mmol),obtained by a procedure as described in Example 25 (Step-1), was added in portions to it. The resulting reaction mixture was stirred for 45 min at 10° C. and a solution of sodium cyanoboro-hydride (0.7 g, 1.1 mmol) in methanol (5 ml) was added dropwise to it. Cooling was removed and stirring was for 24 hr at 30° C. The reaction mixture was basified with 20% KOH solution, filtered (to remove insoluble impurities) and filtrate was concentrated to dryness. The obtained residue was dissolved in water and extracted with chloroform. Chloroform layer was extracted with 50% HCl and acid layer was basified with 20% KOH solution. The separated oil was extracted with chloroform, dried (Na2SO4) and concentrated to give a Mixtures A+B of 4-methylamino-1-carbethoxy-3,5-dimethylpiperidine. Yield 1.34 g (60%), C11H22N2O2, m/z 214 (M+1).

Workup

  1. additionwas added in portions to it
  2. customThe resulting reaction mixture
  3. temperatureCooling
  4. customwas removed
  5. stirringstirring
  6. waitwas for 24 hr at 30° C
  7. filtrationfiltered
  8. custom(to remove insoluble impurities) and filtrate
  9. concentrationwas concentrated to dryness
  10. dissolutionThe obtained residue was dissolved in water
  11. extractionextracted with chloroform
  12. extractionChloroform layer was extracted with 50% HCl and acid layer
  13. extractionThe separated oil was extracted with chloroform
  14. dry with materialdried (Na2SO4)
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-cf5029305ebc4d8a9b397b913be7f3c3
Source dataset
uspto-grants-2005_11
Patent number
US06964966B2

Reaction notes

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