3-Cyclohexylpropylamine → HCID 22141334, compound

HRID 1826407Notes

Reaction equation

HRID 1826407 reaction equation
Cl[CH2:2][CH:3]1[CH:5]([C:6]([O:8]CC)=O)[C:4]1([CH3:20])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1.[CH:21]1([CH2:27][CH2:28][CH2:29][NH2:30])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>Cl>[CH:21]1([CH2:27][CH2:28][CH2:29][N:30]2[CH2:2][CH:3]3[CH:5]([C:4]3([CH3:20])[C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=3)[C:6]2=[O:8])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 126663903-CyclohexylpropylamineHCID 22141336Ethyl 3-(chloromethyl)-2-methyl-2-(3-nitrophenyl)cyclopropanecarboxylate

Product 1

HCID 22141334HCID 22141334, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of ethyl 3-(chloromethyl)-2-methyl-2-(3-nitrophenyl)cyclopropane carboxylate (Preparation 5, 1 g, 3.36 mmol) in 3-cyclohexylpropylamine ([Preparation—Eur. J. Med. Chem. (1992), 27, 321–330], 2.9 g, 20.5 mmol) was heated to 160° C. for 16 h. The mixture was cooled, 2N hydrochloric acid solution (20 ml) was added and the mixture was extracted with dichloromethane (3×20 ml). The combined extracts were dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by silica (200 g) column chromatography eluting with dichloromethane then diethyl ether. Appropriate fractions were combined and concentrated in vacuo to give the title compound as an amber oil (870 mg, 73%).

Workup

  1. temperatureThe mixture was cooled
  2. extractionthe mixture was extracted with dichloromethane (3×20 ml)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica (200 g) column chromatography
  7. washeluting with dichloromethane
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-687118fb9ec14b369f79a51f43b1abcf
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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