Naphthalic anhydride → [3-[[3-(1,3-dioxo-3a,9b-dihydro-1H,3H-benzo[de]isoquinolin-2-yl)propyl]methylamino]propyl]carbamic acid tert-butyl ester

HRID 12258

Reaction equation

HRID 12258 reaction equation
[CH:1]1[CH:2]=[C:3]2[C:8]3=[C:9]([C:11]([O:13][C:14](=[O:15])[C:7]3=[CH:6][CH:5]=[CH:4]2)=O)[CH:10]=1.[C:16]([O:20][C:21](=[O:32])[NH:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:28][CH2:29][CH2:30][NH2:31])[CH3:27])([CH3:19])([CH3:18])[CH3:17]>C(O)C>[C:16]([O:20][C:21](=[O:32])[NH:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:28][CH2:29][CH2:30][N:31]1[C:11](=[O:13])[CH:9]2[CH:10]=[CH:1][CH:2]=[C:3]3[CH:8]2[C:7](=[CH:6][CH:5]=[CH:4]3)[C:14]1=[O:15])[CH3:27])([CH3:19])([CH3:17])[CH3:18]

Participants

4

Reactant 2

HCID 6693Naphthalic anhydrideHCID 12983660tert-butyl N-{3-[(3-aminopropyl)(methyl)amino]propyl}carbamate

Product 1

HCID 86612376[3-[[3-(1,3-dioxo-3a,9b-dihydro-1H,3H-benzo[de]isoquinolin-2-yl)propyl]methylamino]propyl]carbamic acid tert-butyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1,8-naphthalic anhydride (0.18 g, 0.9 mmol) was added to a solution of [3-[(3-aminopropyl)methylamino]propyl]carbamic acid tert-butyl ester previously prepared (Spicer at el., Bioorg. Med. Chem. 2002, vol. 10, p. 19) (0.2 g, 0.8 mmol) in absolute ethanol (20 ml). The reaction mixture was heated at reflux overnight. Removal of the solvent and purification by chromatography on alumina (CH2Cl2/MeOH, 50:1) yielded [3-[[3-(1,3-dioxo-3a,9b-dihydro-1H,3H-benzo[de]isoquinolin-2-yl)propyl]methylamino]propyl]carbamic acid tert-butyl ester (0.37 g, 90%) as a foam.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. customRemoval of the solvent and purification by chromatography on alumina (CH2Cl2/MeOH, 50:1)

Sources & evidence

ORD record
ord-2a5afcdb095849ddb861073e42e5abbe
Source dataset
uspto-grants-2010_06
Patent number
US07728000B2

Linked notes

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