Formic Acid → 4-[(Piperazin-1-yl)methyl]benzonitrile

HRID 905034Notes

Reaction equation

HRID 905034 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6](C=O)=[CH:5][CH:4]=1)#[N:2].[N:11]1([CH:17]=O)[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(O)=O.Cl>C(O)C>[N:11]1([CH2:17][C:6]2[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 660424-CyanobenzaldehydeHCID 821911-Piperazinecarboxaldehyde

Product 1

HCID 20608924-[(Piperazin-1-yl)methyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 13.1 g. of p-cyanobenzaldehyde and 15 ml. of piperazine-1-carboxaldehyde was heated to 100° C. Over 10 minutes, 6 g. of 99% formic acid were added. The mixture was heated for 3 hours, then 200 ml. of 3.6 N hydrochloric acid in ethanol were added and the mixture was refluxed for 4 hours. The solid was collected, washed with ether and suspended in water. 10 N Sodium hydroxide extracted with three 100 ml. portions of chloroform and the combined extracts were evaporated. The residue was suspended in a mixture of 6 N hydrochloric acid and chloroform and filtered. The filtrate was adjusted to pH>7 with 10 N sodium hydroxide, extracted with chloroform, and the extract dried and evaporated to an oil which was distilled, giving α-(1-piperazinyl)-p-tolunitrile as a colorless liquid, b.p. 207°-209° C. (15 mm.).

Workup

  1. additionA mixture of 13.1 g
  2. temperatureThe mixture was heated for 3 hours
  3. temperaturethe mixture was refluxed for 4 hours
  4. customThe solid was collected
  5. washwashed with ether
  6. extraction10 N Sodium hydroxide extracted with three 100 ml
  7. customportions of chloroform and the combined extracts were evaporated
  8. additionThe residue was suspended in a mixture of 6 N hydrochloric acid and chloroform
  9. filtrationfiltered
  10. extractionextracted with chloroform
  11. customthe extract dried
  12. customevaporated to an oil which
  13. distillationwas distilled

Sources & evidence

ORD record
ord-c79e4130a8a24a4daf03e0c6d6ad8b57
Source dataset
uspto-grants-1983_12
Patent number
US04421753

Reaction notes

Loading…