Benzylamine → N-Benzyl-succinamic acid

HRID 1613885Notes

Reaction equation

HRID 1613885 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]1(=[O:15])[O:14][C:12](=[O:13])[CH2:11][CH2:10]1>C1COCC1>[O:15]=[C:9]([NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:10][CH2:11][C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 7922Succinic anhydride

Product 1

HCID 693076N-Benzyl-succinamic acidYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of benzyl amine (10.7 g) and succinic anhydride (10 g) was stirred in THF (1 liter) for 2 days. The solid was filtered and dissolved in 1N NaOH (110 mL). the aqueous phase was washed with Et2O and then made acidic with conc HCl while cooling in an ice-water bath. The solid was collected, washed with water and dried under high vacuum. There was obtained 10.9 g (53%) of the title compound as a white powder m.p. 137.5°-138°.

Workup

  1. filtrationThe solid was filtered
  2. dissolutiondissolved in 1N NaOH (110 mL)
  3. washthe aqueous phase was washed with Et2O
  4. temperaturewhile cooling in an ice-water bath
  5. customThe solid was collected
  6. washwashed with water
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-4156d6e47fab41d6bfdbca5a153af4e6
Source dataset
uspto-grants-1993_03
Patent number
US05194588

Reaction notes

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