1,2-Dichloroethane → Cyclopropanecarboxylic acid cyclopropylamide

HRID 913048Notes

Reaction equation

HRID 913048 reaction equation
[CH:1]1([C:4]([OH:6])=O)[CH2:3][CH2:2]1.[CH:7]1([NH2:10])[CH2:9][CH2:8]1.C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:7]1([NH:10][C:4]([CH:1]2[CH2:3][CH2:2]2)=[O:6])[CH2:9][CH2:8]1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 15655Cyclopropanecarboxylic acidHCID 69828Cyclopropylamine

Product 1

HCID 351205Cyclopropanecarboxylic acid cyclopropylamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a magnetically stirred solution of cyclopropanecarboxylic acid (1.00 g, 11.6 mmol) and cyclopropylamine (0.995 g, 1.5 eq) in 8 mL of methylene chloride was added DMAP (4-dimethylaminopyridine, 2.13 g, 1.5 eq) followed by EDC (1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 3.34 g, 1.5 eq). The reaction was stirred at room temperature for 2 h after which time it was diluted with 50 mL of methylene chloride and washed twice with 0.5 N aqueous HCl followed by water, saturated aqueous sodium bicarbonate, then brine. The solvent was removed under reduced pressure and the residue was purified by silica chromatography eluting with 1:1 hexane/ethyl acetate to afford N-cyclopropylcyclopropanecarboxamide (2-A).

Workup

  1. washwashed twice with 0.5 N aqueous HCl
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by silica chromatography
  4. washeluting with 1:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-f6047136e7cb492f8f27eda65b598020
Source dataset
uspto-grants-2011_09
Patent number
US08026264B2

Reaction notes

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