Sodium Hydroxide → HCID 13534713, compound

HRID 4362Notes

Reaction equation

HRID 4362 reaction equation
Cl.[NH2:2][N:3]1[CH2:8][CH:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.[OH-].[Na+].[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]=[C:25]=[S:26])=[CH:20][CH:19]=1>O1CCOCC1.O>[F:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:2][N:3]2[CH2:4][CH:5]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:7][CH2:8]2)=[S:26])=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 152414-Fluorophenyl isothiocyanateHCID 20152381N-amino-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride

Product 1

HCID 13534713HCID 13534713, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of N-amino-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride (1.05 g) in a mixture of dioxane (10 ml) and water (5 ml) was added 1N sodium hydroxide solution (5 ml) under ice-bath cooling, and then a solution of 4-fluorophenyl isothiocyanate (1.15 g) in dioxane (5 ml) was added thereto. The mixture was stirred for 5 hours under ice-bath cooling. The reaction mixture was evaporated in vacuo and the residue was extracted several times with ethyl acetate. The combined extract was washed with water, dried over magnesium sulfate and evaporated in vacuo to give a crude product, which was recrystallized from ethyl acetate to give N-[[(4-fluorophenyl)thiocarbamoyl]amino]-4-phenyl-1,2,3,6-tetrahydropyridine (1.05 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. customThe reaction mixture was evaporated in vacuo
  4. extractionthe residue was extracted several times with ethyl acetate
  5. extractionThe combined extract
  6. washwas washed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customto give a crude product, which
  10. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-2972a999c99c4df9bc9aa7a812034758
Source dataset
uspto-grants-1988_02
Patent number
US04725608

Reaction notes

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