Ethylamine hydrochloride → 1-Carbethoxy-4-ethylamino-3-methylpiperidine

HRID 1063284

Reaction equation

HRID 1063284 reaction equation
Cl.[CH2:2]([NH2:4])[CH3:3].[C:5]([N:10]1[CH2:15][CH2:14][C:13](=O)[CH:12]([CH3:17])[CH2:11]1)([O:7][CH2:8][CH3:9])=[O:6].[OH-].[K+].C([BH3-])#N.[Na+]>CO>[C:5]([N:10]1[CH2:15][CH2:14][CH:13]([NH:4][CH2:2][CH3:3])[CH:12]([CH3:17])[CH2:11]1)([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 4

HCID 11198Ethylamine hydrochlorideHCID 14797Potassium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 15075657Ethyl 3-methyl-4-oxopiperidine-1-carboxylate

Product 1

HCID 222789001-Carbethoxy-4-ethylamino-3-methylpiperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Ethylamine hydrochloride (5 g, 61.34 mmol) was added to the stirred solution of 1-carbethoxy-3-methyl-4-piperidone (3.5 g, 18.9 mmol) obtained as described in Preparation 1, in methanol (30 ml) followed by 3.43 g (61.34 mmol) KOH. Stirring was continued for 3 hr at ambient temperature. The resulting mixture was cooled at 0° C. and sodium cyanoborohydride (1.4 g, 22.22 mmol) was added to it. Cooling was removed after 10 min. and resulting mixture was stirred for 16 hr at ambient temperature. The reaction mixture was concentrated to dryness, triturated with water, acidified with conc. HCl (pH 3˜4) and extracted with ethyl acetate to remove impurities. The aqueous layer was basified with 1 M sodium hydroxide solution (pH˜10) and extracted with ethyl acetate. Ethyl acetate extract was dried (Na2SO4) and concentrated to dryness to give 1-carbethoxy-4-ethylamino-3-methylpiperidine. Yield 2.3 g (54%), C11H22N2O2, m/z 215 (M+1).

Workup

  1. customobtained
  2. temperatureCooling
  3. customwas removed after 10 min.
  4. customresulting mixture
  5. stirringwas stirred for 16 hr at ambient temperature
  6. concentrationThe reaction mixture was concentrated to dryness
  7. customtriturated with water
  8. extractionextracted with ethyl acetate
  9. customto remove impurities
  10. extractionextracted with ethyl acetate
  11. extractionEthyl acetate extract
  12. dry with materialwas dried (Na2SO4)
  13. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-862c9e1624514928a44601e76a9cda7d
Source dataset
uspto-grants-2005_11
Patent number
US06964966B2

Linked notes

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