Triethylamine → HCID 13534703, compound

HRID 4361

Reaction equation

HRID 4361 reaction equation
Cl.[NH2:2][N:3]1[CH2:8][CH:7]=[CH:6][CH2:5][CH2:4]1.C(N(CC)CC)C.[F:16][C:17]1[CH:18]=[C:19]([N:23]=[C:24]=[O:25])[CH:20]=[CH:21][CH:22]=1>C(Cl)Cl>[F:16][C:17]1[CH:18]=[C:19]([NH:23][C:24]([NH:2][N:3]2[CH2:4][CH:5]=[CH:6][CH2:7][CH2:8]2)=[O:25])[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1230643-Fluorophenyl isocyanateHCID 193760471,2,3,6-Tetrahydropyridin-1-amine hydrochloride

Product 1

HCID 13534703HCID 13534703, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-amino-1,2,3,6-tetrahydropyridine hydrochloride (1.346 g) and triethylamine (1.012 g) in dry methylene chloride (40 ml) was added a solution of 3-fluorophenyl isocyanate (1.37 g) in dry methylene chloride under ice-bath cooling. After stirring for one hour, the reaction mixture was evaporated to dryness. The residue was extracted with ethyl acetate (100 ml). The extract was washed with water, evaporated to dryness and recystallized from ethyl acetate to give N-[[(3-fluorophenyl)carbamoyl]amino]-1,2,3,6-tetrahydropyridine (1.43 g). mp: 136.5°-138.5° C.

Workup

  1. temperaturecooling
  2. customthe reaction mixture was evaporated to dryness
  3. extractionThe residue was extracted with ethyl acetate (100 ml)
  4. washThe extract was washed with water
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-15946ac52f84452daf9d7ce6d8f8fe10
Source dataset
uspto-grants-1988_02
Patent number
US04725608

Linked notes

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