1-Naphthalenemethanamine → HCID 53810492, compound

HRID 1934807Notes

Reaction equation

HRID 1934807 reaction equation
[C:1]([O:10][CH2:11][CH3:12])(=[O:9])/[CH:2]=[CH:3]/[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:13][CH2:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1>C(#N)C>[CH2:11]([O:10][C:1](=[O:9])[CH:2]([NH:13][CH2:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:12]

Participants

4

Reactant 2

HCID 83551-NaphthalenemethanamineHCID 638144Diethyl fumarate

Product 1

HCID 53810492HCID 53810492, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3.12 ml(19.0 mmol) of diethyl fumarate and 3.0 g(19 mmol) of 1-aminomethyl naphthalene were added to acetonitrile, and then the solution was refluxed for 12 hours. Acetonitrile was removed under reduced pressure and column chromatography was performed using a mixed solution of hexane and ethyl acetate(3:1) as an eluent to obtain 4.57 g of the title compound(Yield 73%, MW 329).

Workup

  1. temperaturethe solution was refluxed for 12 hours
  2. customAcetonitrile was removed under reduced pressure and column chromatography

Sources & evidence

ORD record
ord-9d7d97171095480ca7da816c6ac6e760
Source dataset
uspto-grants-2002_05
Patent number
US06384061B1

Reaction notes

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