Naphthalic anhydride → HCID 10040803, compound

HRID 1590042Notes

Reaction equation

HRID 1590042 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.[NH2:16][CH:17]1[CH:22]2[CH2:23][CH2:24][N:19]([CH2:20][CH2:21]2)[CH2:18]1>C(O)CCC>[N:19]12[CH2:24][CH2:23][CH:22]([CH2:21][CH2:20]1)[CH:17]([N:16]1[C:11](=[O:13])[C:9]3[CH:10]=[CH:1][CH:2]=[C:3]4[C:8]=3[C:7](=[CH:6][CH:5]=[CH:4]4)[C:14]1=[O:15])[CH2:18]2

Participants

4

Reactant 2

HCID 6693Naphthalic anhydrideHCID 1232383-Aminoquinuclidine

Product 1

HCID 10040803HCID 10040803, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 1,8-naphthalic anhydride (1.9 g, 9.6 mmol) and (RS)-3-amino-1-azabicyclo[2.2.2]octane (1.2 g, 9.5 mmol) in n-butanol (100 mL) was stirred for 3 hours at reflux temperature and the solution concentrated to dryness. Purification of the remaining solid by column chromatography (silica-gel; 5-10% gradient methanol in CH2Cl2 and approximately 1% aqueous NH4OH) gave (RS)-2-(1-azabicyclo[2.2.2]oct-3-yl)-2,3-dihydro-1H-benz[de]isoquinoline-1,3-dione (2.45 g, 7.95 mmol), m.p. 206°-207° C.

Workup

  1. temperatureat reflux temperature
  2. concentrationthe solution concentrated to dryness
  3. customPurification of the remaining solid by column chromatography (silica-gel; 5-10% gradient methanol in CH2Cl2 and approximately 1% aqueous NH4OH)

Sources & evidence

ORD record
ord-10f1d572b2894f119795f84849b05e25
Source dataset
uspto-grants-1993_04
Patent number
US05202318

Reaction notes

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