Cyclopropylamine → HCID 22278922, compound

HRID 1063286Notes

Reaction equation

HRID 1063286 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][C:13]([C:5]([O:7][CH2:8][CH3:9])=[O:6])([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 22278922HCID 22278922, 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-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-fc2214bd2b284fa585b8482b9c8f607c
Source dataset
uspto-grants-2005_11
Patent number
US06964966B2

Reaction notes

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