Cyclopropylamine → HCID 22278896, compound

HRID 1865227Notes

Reaction equation

HRID 1865227 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[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].C([BH3-])#N.[Na+]>CO>[C:5]([N:10]1[CH2:15][CH2:14][CH:13]([NH:4][CH:1]2[CH2:3][CH2:2]2)[CH:12]([CH3:17])[CH2:11]1)([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 5003444Sodium cyanoborohydrideHCID 15075657Ethyl 3-methyl-4-oxopiperidine-1-carboxylate

Product 1

HCID 22278896HCID 22278896, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Cyclopropylamine (10 g, 169.5 mmol) was added to the stirred solution of 1-carbethoxy-3-methyl-4-piperidone (7.0 g, 37.83 mmol) obtained as described in Preparation 1, in methanol (50 ml) and stirring was continued for 12 hr at ambient temperature. The resulting mixture was cooled at 0° C. and sodium cyanoborohydride (3.0 g, 46.0 mmol) was added to it. Cooling was removed after 10 min. and stirring was continued for 12 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 afford 1-carbethoxy-4-cyclopropylamino-3-methylpiperidine. Yield 6.0 g (70%), C12H22N2O2, m/z 227 (M+1), PMR (CDCl3): 0.38 (m, 4H), 0.88 (dd, 3H), 1.28 (t, 3H), 1.54 (m, 1H), 2.06 (m, 2H), 2.32 (m, 1H), 2.48 (m, 1H), 2.84 (m, 1H), 3.06 (m, 1H), 3.72 (m, 1H), 3.88-4.24 (m, 2H).

Workup

  1. customobtained
  2. temperatureCooling
  3. customwas removed after 10 min.
  4. stirringstirring
  5. waitwas continued for 12 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-5df802c19ba34faa85e9685ffd6971c8
Source dataset
uspto-grants-2009_12
Patent number
US07626032B2

Reaction notes

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