Water → N-[[(4-fluorophenyl)carbamoyl]amino]-1,2,3,6-tetrahydropyridine

HRID 4365Notes

Reaction equation

HRID 4365 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:11]=[N+:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH2:13]2)=[O:10])=[CH:4][CH:3]=1.[BH4-].[Na+].O>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][N:12]2[CH2:13][CH:14]=[CH:15][CH2:16][CH2:17]2)=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydride2×HCID 20152379N-[[(4-fluorophenyl)carbamoyl]-imino]pyridinium

Product 1

HCID 13534699N-[[(4-fluorophenyl)carbamoyl]amino]-1,2,3,6-tetrahydropyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of N-[[(4-fluorophenyl)carbamoyl]-imino]pyridinium ylide (1.04 g) and sodium borohydride (2.55 g) in ethanol (100 ml) was stirred at ambient temperature for 16 hours. Excess of sodium borohydride was decomposed with water, and the resulting mixture was evaporated. The residue was extracted with chloroform (20 ml×3). The combined organic extract was washed with water, dried over magnesium sulfate and evaporated to give crystalls. Recrystallization from diisopropyl ether gave N-[[(4-fluorophenyl)-carbamoyl]amino]-1,2,3,6-tetrahydropyridine (0.60 g).

Workup

  1. customthe resulting mixture was evaporated
  2. extractionThe residue was extracted with chloroform (20 ml×3)
  3. extractionThe combined organic extract
  4. washwas washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customto give crystalls
  8. customRecrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-ba8e9518e9a14e998c41606e7292d98b
Source dataset
uspto-grants-1988_02
Patent number
US04725608

Reaction notes

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