Oxalic Acid → 8-{2-[3-(2-Naphthyl)-8-azabicyclo[3.2.1]oct-8-yl]ethoxy}quinoline

HRID 987586Notes

Reaction equation

HRID 987586 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.CO[C:14]1[CH:15]=[C:16]2[C:21](=[C:22](O)[CH:23]=1)[N:20]=[CH:19][CH:18]=[CH:17]2.[C:25](O)(=O)[C:26](O)=O>CN(C=O)C>[CH:21]1[C:22]2[C:23](=[CH:11][CH:2]=[CH:3][CH:4]=2)[CH:14]=[CH:15][C:16]=1[CH:17]1[CH2:8][CH:7]2[N:20]([CH2:25][CH2:26][O:1][C:2]3[CH:3]=[CH:4][CH:5]=[C:6]4[C:11]=3[N:10]=[CH:9][CH:8]=[CH:7]4)[CH:19]([CH2:5][CH2:6]2)[CH2:18]1

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 19238-HydroxyquinolineHCID 180091706-Methoxyquinolin-8-ol

Product 1

HCID 102015188-{2-[3-(2-Naphthyl)-8-azabicyclo[3.2.1]oct-8-yl]ethoxy}quinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound is prepared according to Example 8, Step 5, except 8-hydroxyquinoline is used in place 6-methoxyquinolin-8-ol. The corresponding oxalate salt is prepared by treating the title compound with 1 equiv. oxalic acid in DMF to precipitate a white solid. Yield: 51%; mp: 110-113° C.; MS (ES) m/z: 409 (MH)+.

Workup

  1. customThe title compound is prepared
  2. customto precipitate a white solid

Sources & evidence

ORD record
ord-a697807a9ca2483d89acf66924cb416c
Source dataset
uspto-grants-2003_10
Patent number
US06632824B2

Reaction notes

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