Ethylamine hydrochloride → 4-Ethylamino-1-carbethoxy-3,5-dimethylpiperidine

HRID 1865269Notes

Reaction equation

HRID 1865269 reaction equation
[OH-].[K+].Cl.[CH2:4]([NH2:6])[CH3:5].[C:7]([N:12]1[CH2:17][CH:16]([CH3:18])[C:15](=O)[CH:14]([CH3:20])[CH2:13]1)([O:9][CH2:10][CH3:11])=[O:8].C([BH3-])#N.[Na+]>CO>[CH2:4]([NH:6][CH:15]1[CH:16]([CH3:18])[CH2:17][N:12]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:13][CH:14]1[CH3:20])[CH3:5]

Participants

6

Reactant 4

HCID 11198Ethylamine hydrochlorideHCID 14797Potassium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 222788871-Carbethoxy-3,5-dimethyl-4-piperidinone

Product 1

HCID 222789054-Ethylamino-1-carbethoxy-3,5-dimethylpiperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Powdered KOH (2.8 g, 50 mmol) was added in portions to the stirred solution of ethylamine hydrochloride (4.0 g, 50 mmol) in methanol (50 ml) and 1-carbethoxy-3,5-dimethyl-4-piperidinone (5.0 g, 25.12 mmol) obtained by a procedure as described in Example 25 (Step-1), was added to it. The resulting reaction mixture was stirred for 6 hr. A solution of sodium cyanoborohydride (1.6 g, 25.12 mmol) in methanol (10 ml) was added dropwise to it and stirring was continued for 16 hr. The reaction mixture 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 KOH (20%) solution. The oil thus separated was extracted with chloroform, dried (Na2SO4) and concentrated to give Mixtures A+B of 4-ethylamino-1-carbethoxy-3,5-dimethylpiperidine as an oil. Yield 5.6 g (97.7%),−C12H24N2O2, m/z 229 (M+1).

Workup

  1. customobtained by a procedure
  2. additionwas added to it
  3. customThe resulting reaction mixture
  4. stirringstirring
  5. waitwas continued for 16 hr
  6. concentrationThe reaction mixture was concentrated to dryness
  7. dissolutionThe obtained residue was dissolved in water
  8. extractionextracted with chloroform
  9. extractionChloroform layer was extracted with 50% HCl and acid layer
  10. customThe oil thus separated
  11. extractionwas extracted with chloroform
  12. dry with materialdried (Na2SO4)
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-0f497b3d53fb46d89f30ab56b54f88ff
Source dataset
uspto-grants-2009_12
Patent number
US07626032B2

Reaction notes

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