Cyclopropanecarboxylic acid → N-(Cyclopropylmethyl)cyclopropanecarboxamide

HRID 1170433Notes

Reaction equation

HRID 1170433 reaction equation
[CH:1]1([C:4]([OH:6])=O)[CH2:3][CH2:2]1.[CH:7]1([CH2:10][NH2:11])[CH2:9][CH2:8]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C>[CH:7]1([CH2:10][NH:11][C:4]([CH:1]2[CH2:3][CH2:2]2)=[O:6])[CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 15655Cyclopropanecarboxylic acidHCID 75646CyclopropanemethanamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 21916069N-(Cyclopropylmethyl)cyclopropanecarboxamideYield 42%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of cyclopropane carboxylic acid (1.72 g, 20 mmol) and cyclopropylmethylamine (1.42 g, 20 mmol) in N,N-dimethylformamide (20 mL) were added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.22 g, 22 mmol) and 1-hydroxybenzotriazole (4.05 mmol, 30 mmol), and the mixture was stirred at room temperature for 20 hours. To the reaction solution was added ethyl acetate, and the mixture was washed with 1M hydrochloric acid and saturated aqueous sodium bicarbonate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The resulting residue was recrystallized (diethyl ether-n-hexane) to give the titled compound (1.16 g, 42%).

Workup

  1. washthe mixture was washed with 1M hydrochloric acid and saturated aqueous sodium bicarbonate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was recrystallized (diethyl ether-n-hexane)

Sources & evidence

ORD record
ord-6ab5e7dc92464636b9e0685e8341eb18
Source dataset
uspto-grants-2010_11
Patent number
US07825155B2

Reaction notes

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