Ammonia → 2-(3-Cyanopropyl)-4-dimethylaminomethylpyridine

HRID 851488

Reaction equation

HRID 851488 reaction equation
S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+].[C:13]([CH2:15][CH2:16][CH2:17][C:18](O)=O)#[N:14].[CH3:21][N:22]([CH2:24][C:25]1[CH:30]=C[N:28]=[CH:27][CH:26]=1)[CH3:23].S(=O)(=O)(O)O.N>O.[N+]([O-])([O-])=O.[Ag+]>[C:13]([CH2:15][CH2:16][CH2:17][C:18]1[CH:30]=[C:25]([CH2:24][N:22]([CH3:23])[CH3:21])[CH:26]=[CH:27][N:28]=1)#[N:14]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 382394-Cyanobutanoic acidHCID 62648Ammonium PersulfateHCID 2649464-pyridinemethanamine, N,N-dimethyl-

Product 1

HCID 132926072-(3-Cyanopropyl)-4-dimethylaminomethylpyridineYield 36.9%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent3×

Procedure

Ammonium persulphate (54.8 g) in water (150 ml) and 4-cyanobutyric acid (68 g) in water (300 ml) were added separately and simultaneously over 30 minutes to a mixture of 4-dimethylaminomethylpyridine (16.32 g), silver nitrate (4 g), water (200 ml) and concentrated sulphuric acid (25 ml) stirred at 80°. The reaction mixture was stirred at 80° for 1.5 hours, cooled, poured onto crushed ice (400 g) and aqueous ammonia (28% w/w, 200 ml). The solution was extracted with chloroform (900 ml) and the chloroform extracts were washed with dilute sodium hydroxide, dried over magnesium sulphate, and concentrated in vacuo to give 2-(3-cyanopropyl)-4-dimethylaminomethylpyridine (9 g) as a clear oil b.p. 110°-112°/0.1 mm Hg.

Workup

  1. stirringThe reaction mixture was stirred at 80° for 1.5 hours
  2. temperaturecooled
  3. additionpoured
  4. extractionThe solution was extracted with chloroform (900 ml)
  5. washthe chloroform extracts were washed with dilute sodium hydroxide
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9709cc2b9a614ec69102f7b1aa3416fc
Source dataset
uspto-grants-1983_05
Patent number
US04385058

Linked notes

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