Hydrochloric Acid → HCID 20216139, compound

HRID 236546Notes

Reaction equation

HRID 236546 reaction equation
[NH:1]1[CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1.[C:7]([C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11]Br)#[N:8].C(=O)([O-])[O-].[K+].[K+].[ClH:23]>C(O)C>[ClH:23].[C:7]([C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11][N:1]1[CH2:2][CH:3]=[CH:4][CH2:5][CH2:6]1)#[N:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 127501,2,3,6-TetrahydropyridineHCID 895992-(Bromomethyl)benzonitrile

Product 1

HCID 20216139HCID 20216139, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1,2,3,6-Tetrahydropyridine (5.0 g.) was added to a mixture of 2-cyanobenzyl bromide (11.8 g.) and potassium carbonate (9.16 g.) in ethanol (80 ml.). The mixture obtained was heated under reflux for 2.5 hours, cooled and evaporated. Water (120 ml.) was added to the residue and the oily mixture obtained was extracted with ether (3×50 ml.). The combined extracts were washed with water, dried (MgSO4) and evaporated. The residue oil was dissolved in toluene (20 ml.) to give a solution, which was treated with a slight excess of methanolic hydrogen chloride. The mixture was evaporated and the solid residue which was left was triturated with acetone, collected by filtration, and recrystallised from a mixture of ethanol and ethyl acetate to give 1-(2-cyanobenzyl)-1,2,3,6-tetrahydropyridine hydrochloride, as colourless needles (7.1 g), m.p. 219°-221° C.

Workup

  1. customThe mixture obtained
  2. temperaturewas heated
  3. temperatureunder reflux for 2.5 hours
  4. temperaturecooled
  5. customevaporated
  6. additionWater (120 ml.) was added to the residue
  7. customthe oily mixture obtained
  8. extractionwas extracted with ether (3×50 ml.)
  9. washThe combined extracts were washed with water
  10. dry with materialdried (MgSO4)
  11. customevaporated
  12. dissolutionThe residue oil was dissolved in toluene (20 ml.)
  13. customto give a solution, which
  14. customThe mixture was evaporated
  15. waitthe solid residue which was left
  16. customwas triturated with acetone
  17. filtrationcollected by filtration
  18. customrecrystallised from a mixture of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-8169556be74644ff89ce4f5fa24a0459
Source dataset
uspto-grants-1987_02
Patent number
US04645771

Reaction notes

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