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

HRID 4360

Reaction equation

Cl.[NH2:2][N:3]1[CH2:8][CH:7]=[CH:6][CH2:5][CH2:4]1.[OH-].[Na+].[F:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=[O:20])=[CH:14][CH:13]=1>O1CCOCC1.O>[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([NH:2][N:3]2[CH2:4][CH:5]=[CH:6][CH2:7][CH2:8]2)=[O:20])=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 5 °C

Procedure

N-Amino-1,2,3,6-tetrahydropyridine hydrochloride (3.42 g) was dissolved in a mixture of dioxane (30 ml) and water (20 ml). The solution was adjusted to pH 7.5 with 1N-aqueous sodium hydroxide and to the resultant mixture was added a solution of 4-fluorophenylisocyanate (0.548 g) in dioxane (5 ml). Then, the mixture was kept to pH 7.5 and stirred for 2 hours at 5° C. After evaporation of organic solvent, the crystalline product was collected by filtration and recrystallized from diisopropyl ether to give white needles of N-[[(4-fluorophenyl)carbamoyl]amino]-1,2,3,6-tetrahydropyridine (0.73 g). mp: 156°-157° C.

Workup

customAfter evaporation of organic solvent
filtrationthe crystalline product was collected by filtration
customrecrystallized from diisopropyl ether

Sources & evidence

ORD record: ord-a3795389ab974dca90679ddbd9c6c680
Source dataset: uspto-grants-1988_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04725608

Linked notes

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