Sulfuric Acid → Butyl 3-[benzyl(cyanomethyl)amino]butanoate

HRID 1762945Notes

Reaction equation

HRID 1762945 reaction equation
[CH2:1]([N:8]([CH:12]([CH3:17])[CH2:13][C:14]([OH:16])=[O:15])[CH2:9][C:10]#[N:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O>C(O)CCC>[CH2:1]([O:15][C:14](=[O:16])[CH2:13][CH:12]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][C:10]#[N:11])[CH3:17])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 132421993-[Benzyl(cyanomethyl)amino]butanoic acid

Product 1

HCID 13242200Butyl 3-[benzyl(cyanomethyl)amino]butanoateYield 41%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 4.6 g of 3-(N-benzyl-N-cyanomethylamino)butyric acid in 100 ml of n-butanol is combined with 0.5 ml of concentrated sulfuric acid and the mixture is heated for 4 hours on a water trap under reflux. The reaction mixture is allowed to cool, concentrated to dryness, and the residue dissolved in diethyl ether. The ether solution is washed with 10% sodium bicarbonate solution and saturated sodium chloride solution, dried, and evaporated to dryness. The oily residue is distilled in a bulb tube at 85°-105° C. and 0.01 torr, thus obtaining 1.17 g of 3-(N-benzyl-N-cyanomethylamino)butyric acid n-butyl ester as an oil.

Workup

  1. temperaturethe mixture is heated for 4 hours on a water trap
  2. temperatureunder reflux
  3. temperatureto cool
  4. concentrationconcentrated to dryness
  5. dissolutionthe residue dissolved in diethyl ether
  6. washThe ether solution is washed with 10% sodium bicarbonate solution and saturated sodium chloride solution
  7. customdried
  8. customevaporated to dryness
  9. distillationThe oily residue is distilled in a bulb tube at 85°-105° C.

Sources & evidence

ORD record
ord-6a8de2c853ab478aba4820e6d83e3bd8
Source dataset
uspto-grants-1989_05
Patent number
US04835175

Reaction notes

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