Cyclopropylamine → Ethyl 4-(cyclopropylamino)cyclohexanecarboxylate

HRID 1025415Notes

Reaction equation

HRID 1025415 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O=[C:20]1[CH2:25][CH2:24][CH:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.ClCCCl.C(O)(=O)C>[CH:1]1([NH:4][CH:20]2[CH2:25][CH2:24][CH:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]2)[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 69828CyclopropylamineHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67126892Ethyl 4-(cyclopropylamino)cyclohexanecarboxylateYield 90.5%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

To a mixture of 3.35 g of cyclopropylamine, 1.0 mL of acetic acid, 9.34 g of sodium triacetoxyborohydride, and 30 mL of 1,2-dichloroethane was added dropwise 5.00 g of ethyl 4-oxocyclohexane carboxylate at room temperature. After stirring at room temperature for 14 hours, to the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution to quench the reaction. To the reaction mixture was added chloroform, followed by extraction and then the organic layer was dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (aqueous ammonia-methanol-chloroform) to obtain 5.62 g of ethyl 4-(cyclopropylamino)cyclohexane carboxylate as a colorless oily substance.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionfollowed by extraction
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (aqueous ammonia-methanol-chloroform)

Sources & evidence

ORD record
ord-7fd9576ce5364ebea71ef76111132f1c
Source dataset
uspto-grants-2014_05
Patent number
US08729068B2

Reaction notes

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