Sodium Hydroxide → HCID 13561521, compound

HRID 485088Notes

Reaction equation

HRID 485088 reaction equation
[C:1]([N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16])(OCC)=O.[OH-:17].[Na+]>>[C:7]1(=[O:16])[N:6]([CH2:1][C@@H:13]2[CH2:14][CH2:15][CH:8]=[CH:7][O:17]2)[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]12

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 31187N-Carbethoxyphthalimide

Product 1

HCID 13561521HCID 13561521, compound

Procedure

The amine tartrate (107.0 g, 407 mmol) was added to 4N sodium hydroxide (310 mL) and extracted with ether (3×100 mL). The ether was dried over anhydrous sodium sulfate and evaporated in vacuo. The amine which remained was dissolved in tetrahydrofuran (450 mL). With stirring, N-carboethoxyphthalimide (89.60 g, 409 mmol) was added to the solution. The mixture was refluxed overnight then evaporated in vacuo. The residue was taken up into benzene (660 mL) and water (180 mL). The layers were separated and the organic layer was washed with water (180 mL), 5% sodium hydroxide (180 mL), water (2×180 mL), and saturated brine (180 mL). The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo leaving the crude product (97.0 g) as a white solid. This was recrystallized from ether-petroleum ether (1:1). Yield 72.64 g (73%), m.p. 87°-88° C.; Anal. Calcd. for C14H13NO3 : C, 69.12 ; H, 5.39; N, 5.76. Found: C, 69.18; H, 5.36; N, 5.66.

Workup

  1. extractionextracted with ether (3×100 mL)
  2. dry with materialThe ether was dried over anhydrous sodium sulfate
  3. customevaporated in vacuo
  4. dissolutionThe amine which remained was dissolved in tetrahydrofuran (450 mL)
  5. temperatureThe mixture was refluxed overnight
  6. customthen evaporated in vacuo
  7. customThe layers were separated
  8. washthe organic layer was washed with water (180 mL), 5% sodium hydroxide (180 mL), water (2×180 mL), and saturated brine (180 mL)
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-e91ad79a8e5f4081889e5c746a14176a
Source dataset
uspto-grants-1985_08
Patent number
US04535169

Reaction notes

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