Norbornadiene → N-(3,4-dichlorophenyl)-4-({(3R)-1-[2-(1H-1,2,3-triazol-1-yl)ethyl]piperidin-3-yl}methyl)piperazine-1-carboxamide

HRID 603219Notes

Reaction equation

[N:1]([CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][C@@H:8]([CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=3)=[O:20])[CH2:15][CH2:14]2)[CH2:7]1)=[N+:2]=[N-:3].[CH:30]12CC(C=C1)C=[CH:31]2>O1CCOCC1>[Cl:29][C:24]1[CH:23]=[C:22]([NH:21][C:19]([N:16]2[CH2:17][CH2:18][N:13]([CH2:12][C@@H:8]3[CH2:9][CH2:10][CH2:11][N:6]([CH2:5][CH2:4][N:1]4[CH:31]=[CH:30][N:3]=[N:2]4)[CH2:7]3)[CH2:14][CH2:15]2)=[O:20])[CH:27]=[CH:26][C:25]=1[Cl:28]

Participants

Conditions

Temperature: 180 °C

Procedure

4-{[(3R)-1-(2-Azidoethyl)piperidin-3-yl]methyl}-N-(3,4-dichlorophenyl)piperazine-1-carboxamide (100 mg, 0.23 μmmol) was dissolved in 1,4-dioxane (4 ml). Bicyclo(2.2.1)hepta-2,5-diene (0.5 ml) was added and the mixture heated in the microwave at 180° C. for 20 minutes. The reaction mixture was poured onto a bond elute column (SiO2, 20 g) and the product eluted with a gradient of dichloromethane through to 20% methanolic ammonia/dichloromethane to yield the title compound as a white solid (80.1 mg)

Workup

additionThe reaction mixture was poured onto a bond
washelute column (SiO2, 20 g)
washthe product eluted with a gradient of dichloromethane through to 20% methanolic ammonia/dichloromethane

Sources & evidence

ORD record: ord-b9d4a93abbd4432e89718d1d8dbb8837
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906645B2

Reaction notes

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