Hydrochloric Acid → N-(phenylcarbamoylamino)-1,2,3,6-tetrahydropyridine

HRID 4364Notes

Reaction equation

HRID 4364 reaction equation
[C:1]1([NH:7][C:8]([N:10]=[N+:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].Cl>C(O)C.O>[C:1]1([NH:7][C:8]([NH:10][N:11]2[CH2:12][CH:13]=[CH:14][CH2:15][CH2:16]2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 20152386N-(phenylcarbamoylimino)pyridinium

Product 1

HCID 13534718N-(phenylcarbamoylamino)-1,2,3,6-tetrahydropyridine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of N-(phenylcarbamoylimino)pyridinium ylide (0.64 g) in a mixture of ethanol (30 ml) and water (10 ml) was added sodium borohydride (0.20 g) at ambient temperature. After being stirred for 4 hours, the reaction mixture was acidified with 1N hydrochloric acid, concentrated to a volume of ca. 15 ml. The crystalline precipitate was collected, washed with water and dried in vacuo. The crude product was dissolved in ethyl acetate and extracted with 10% hydrochloric acid (20 ml). The extract was adjusted to pH 3 with aqueous sodium bicarbonate and extracted with ethyl acetate (30 ml). The organic layer was washed with aqueous sodium bicarbonate (10 ml), dried over magnesium sulfate and evaporated to give N-(phenylcarbamoylamino)-1,2,3,6-tetrahydropyridine (0.28 g), which was recrystallized from ethyl acetate to afford colorless needles (0.15 g). mp: 157°-159° C.

Workup

  1. concentrationconcentrated to a volume of ca. 15 ml
  2. customThe crystalline precipitate was collected
  3. washwashed with water
  4. customdried in vacuo
  5. dissolutionThe crude product was dissolved in ethyl acetate
  6. extractionextracted with 10% hydrochloric acid (20 ml)
  7. extractionextracted with ethyl acetate (30 ml)
  8. washThe organic layer was washed with aqueous sodium bicarbonate (10 ml)
  9. dry with materialdried over magnesium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-4dac31e8682a4872921ace479cd32233
Source dataset
uspto-grants-1988_02
Patent number
US04725608

Reaction notes

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