Acetone → N-benzyl-N-(2-cyanoethyl)-4-aminobutan-2-one

HRID 1576504Notes

Reaction equation

HRID 1576504 reaction equation
[C:1]([CH2:3][CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)#[N:2].Cl.[CH2:14](O)C.C=O.[CH3:19][C:20]([CH3:22])=[O:21]>>[CH2:6]([N:5]([CH2:4][CH2:3][C:1]#[N:2])[CH2:14][CH2:19][C:20](=[O:21])[CH3:22])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 5

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 702EthanolHCID 712FormaldehydeHCID 697193-(Benzylamino)propionitrile

Product 1

HCID 21453215N-benzyl-N-(2-cyanoethyl)-4-aminobutan-2-one

Procedure

A mixture of β-cyanoethylbenzylamine (92g.), conc hydrochloric acid (60 ml.), ethanol (120 ml.), paraformaldehyde (30 g.) and acetone (120 ml.) were heated at reflux for 5 hours. The solvent was removed in vacuo and the residue dissolved in water (100 ml.) and washed with ether (2 × 100 ml.). The aqueous solution was made basic with aqueous potassium carbonate and the solution extracted with ether (3 × 100 ml.). The combined extracts were dried and evaporated to give N-benzyl-N-(2-cyanoethyl)-4-aminobutan-2-one(132 g) which was dissolved in dry benzene (1.3 liter) and sodium methoxide (prepared from sodium (13.2g) was added portionwise. The mixture was refluxed for 5 hours and the cooled solution washed with 2N HCl (4 × 500 ml.). The combined extracts were made basic with potassium carbonate and extracted into methylene chloride (4 × 500 ml.) and the combined extracts dried (MgSO4) and solvent removed in vacuo. The residual oil was distilled to give 1-benzyl-3-cyano-4-methyl-1,2,5,6-tetrahydropyridine as a colourless oil (40 g.) b.p. 136°C/5 × 10-3 mm. Hg. which was converted to the hydrochloride by treating an ethereal solution with dry HCl gas. The resultant solid was recrystallised from methanol-ether giving the hydrochloride of the title compound as colourless needles (35 g.) m.p. 172°C. Found: C,68.0; H, 7.0; N, 11.3% C14H16N2HCl requires C, 67.6; H, 6.9; N, 11.3%.

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 5 hours
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue dissolved in water (100 ml.)
  5. washwashed with ether (2 × 100 ml.)
  6. extractionthe solution extracted with ether (3 × 100 ml.)
  7. customThe combined extracts were dried
  8. customevaporated

Sources & evidence

ORD record
ord-4eb1651dd23745869019c67cdc74b2de
Source dataset
uspto-grants-1976_09
Patent number
US03981878

Reaction notes

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