Succinic anhydride → N-Benzyloxy-N-(4-cyanobutyl)succinamic acid

HRID 1656817Notes

Reaction equation

HRID 1656817 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][NH:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)#[N:2].[C:16]1(=[O:22])[O:21][C:19](=[O:20])[CH2:18][CH2:17]1>N1C=CC=CC=1>[CH2:9]([O:8][N:7]([CH2:6][CH2:5][CH2:4][CH2:3][C:1]#[N:2])[C:16](=[O:22])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 14078488O-Benzyl-N-(4-cyanobutyl)hydroxylamine

Product 1

HCID 10990339N-Benzyloxy-N-(4-cyanobutyl)succinamic acidYield 98.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

N-Benzyloxy-N-(4-cyanobutyl)succinamic acid (6) was synthesized by charging a flask with 2.8 g (13.7 mmol) of (5) in 23 mL of pyridine and 2.1 g (20.8 mmol) of succinic anhydride, heated at 100° C. for 1.5 hours and then allowed to cool to room temperature and to stir overnight. The pyridine was removed under vacuum and the residue was dissolved in a is minimal amount of chloroform and filtered. The chloroform was removed and the residue was dissolved in ether, which was extracted three times with 20% potassium bicarbonate (3×50 mL). The aqueous solutions were combined, acidified and extracted with ether. This solution was dried over anhydrous sodium sulfate, filtered and evaporated. The residue was then chromatographed on 70-230 mesh silica gel by eluting with 5% methanol in chloroform to give 4.12 g (98%) of (6): NMR δ 1.56-1.7 (m, 2 H), 1.7-1.97 (m, 2 H), 2.36 (to 2 H), 2.60-2.80 (m, 4 H); 3.68 (t, 2 H), 4.85 (s, 2 H), 7.4 (s, 5 H); IR (CHCl3) 3670, 2930, 2240, 1710, 1650, 1415, 1200 cm-1. Anal. calcd. for C16H20N2O4 : C, 63.17; H, 6.64. Found: C, 63.36; H, 6.74. A sample of (6) was crystallized from hexane/EtoAc, mp 71° C.

Workup

  1. customN-Benzyloxy-N-(4-cyanobutyl)succinamic acid (6) was synthesized
  2. temperatureto cool to room temperature
  3. customThe pyridine was removed under vacuum
  4. dissolutionthe residue was dissolved in a is minimal amount of chloroform
  5. filtrationfiltered
  6. customThe chloroform was removed
  7. dissolutionthe residue was dissolved in ether
  8. extractionwhich was extracted three times with 20% potassium bicarbonate (3×50 mL)
  9. extractionextracted with ether
  10. dry with materialThis solution was dried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. customevaporated
  13. customThe residue was then chromatographed on 70-230 mesh silica gel
  14. washby eluting with 5% methanol in chloroform

Sources & evidence

ORD record
ord-bf35553292454e2f889f603403c29fe1
Source dataset
uspto-grants-1993_10
Patent number
US05254724

Reaction notes

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