Pyridine, 1,4-dihydro-1-methyl- → 2-Methyl-7-[(4-aminophenyl)sulfonyl]-2,7-diazabicyclo[4.1.0]hept-3-ene

HRID 358453Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]=[N+]=[N-])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:14][N:15]1[CH:20]=[CH:19][CH2:18][CH:17]=[CH:16]1>CCOCC>[CH3:14][N:15]1[CH:16]=[CH:17][CH2:18][CH:19]2[CH:20]1[N:11]2[S:8]([C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 4-aminobenzenesulfonyl azide (0.63 g, 3.2 mmol) in 75 ml ether was added slowly to a solution of 1-methyl-1,4-dihydropyridine (0.30 g, 3.2 mmol) in 75 ml ether with stirring at 25° C. Evolution of nitrogen gas was immediate. The reaction was allowed to proceed for 2 hours and the solvent was removed in vacuo to give 2-methyl-7-[(4-aminophenyl)sulfonyl]-2,7-diazabicyclo[4.1.0]hept-3-ene (0.82 g, 97%) with mp 188-190° . Hydrogenation of 2-methyl-7-[(4-aminophenyl) sulfonyl]-2,7-diazbicyclo[4.1.0]hept-3-ene (33 mg, 0.117 mmol) in 15 ml ethanol was effected using 10% palladium on charcoal (15 mg) and hydrogen gas at 30 psi for 4 hours. Removal of the catalyst by filtration and evaporation of the solvent in vacuo gave 1-methylpiperidylidene-2-(4-aminophenyl)sulfonamide (31 mg, 93%) with mp 186-188° ; IR (KBr) 3480 and 3380 cm-1 (NH2) and 1590 cm-1 (C=N).

Workup

customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-5182d72416fb47498a647c9ed89caca6
Source dataset: uspto-grants-1984_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04468403

Reaction notes

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