Phthalic Anhydride → HCID 69194491, compound

HRID 747836Notes

Reaction equation

HRID 747836 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C:11]23[CH2:20][CH:15]([CH2:16][CH:17]([NH2:19])[CH2:18]2)[N:14]([CH3:21])[CH2:13][CH:12]3[CH3:22])[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].[C:23]1(=O)[O:28][C:26](=[O:27])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]12>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C:11]23[CH2:20][CH:15]([CH2:16][CH:17]([N:19]4[C:26](=[O:27])[C:25]5[C:24](=[CH:32][CH:31]=[CH:30][CH:29]=5)[C:23]4=[O:28])[CH2:18]2)[N:14]([CH3:21])[CH2:13][CH:12]3[CH3:22])[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6811Phthalic AnhydrideHCID 69194495HCID 69194495, compound

Product 1

HCID 69194491HCID 69194491, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(3-Isopropoxy-phenyl)-2,4-dimethyl-2-aza-bicyclo[3.3.1 ]non-7-ylamine (2.4) (1.69 g, 5.6 mmol) was dissolved in toluene followed by the addition of phthalic anhydride (2.5 g, 16.8 mmol) and the reaction mixture was refluxed with a Dean-Stark trap overnight. The solution was then cooled, diluted with ethyl acetate, and filtered into a separatory funnel. The organic layer was washed with 1 N NaOH (3×30 ml) and water. The organic layer was collected, dried (Na2SO4) and the solvent removed under reduced pressure yielding crude product. The crude product was purified by filtering through a short column of neutral alumina (Brockman activity II-III) eluting with ethyl acetate to afford the title compound (1.50 g, 62%) as an off white solid. 1H NMR (CDCl3) δ: 7.76 (m, 2H), 7.65 (m, 2H), 7.23 (t, 1H, J=7.8), 7.00-6.72 (m, 3H), 5.08 (m, 1H), 4.52 (sept., 1H, J=6.1 Hz), 3.15 (m, 1H), 2.96 (m, 1H), 2.62 (m, 1H), 2.45-2.32 (m, 4H), 2.23 (s, 1H), 2.11 (m, 1H), 1.67 (m, 2H), 1.31 (d, 6H, J=6.0 Hz), 1.15 (m, 1H), 0.94 (m, 1H), 0.73 (d, 3H, J=6.9 Hz).

Workup

  1. temperaturethe reaction mixture was refluxed with a Dean-Stark trap overnight
  2. temperatureThe solution was then cooled
  3. filtrationfiltered into a separatory funnel
  4. washThe organic layer was washed with 1 N NaOH (3×30 ml) and water
  5. customThe organic layer was collected
  6. dry with materialdried (Na2SO4)
  7. customthe solvent removed under reduced pressure
  8. customyielding crude product
  9. customThe crude product was purified
  10. filtrationby filtering through a short column of neutral alumina (Brockman activity II-III)
  11. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-4c885e4d0d0549b38cedb8ee3fbeb370
Source dataset
uspto-grants-2008_07
Patent number
US07399762B2

Reaction notes

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