Piperidine → 1-{3-[3-(Methyloxy)-4-nitrophenyl]-2-propyn-1-yl}piperidine

HRID 419480Notes

Reaction equation

Cl[CH2:2][C:3]#[C:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([O:14][CH3:15])[CH:6]=1.[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>O1CCOCC1>[CH3:15][O:14][C:7]1[CH:6]=[C:5]([C:4]#[C:3][CH2:2][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:10]=[CH:9][C:8]=1[N+:11]([O-:13])=[O:12]

Participants

Conditions

Temperature: 110 °C

Procedure

To 4-(3-chloro-1-propyn-1-yl)-2-(methyloxy)-1-nitrobenzene (0.250 g, 1.1 mmol) in 10 mL of dioxane was added, piperidine (0.26 g, 3.1 mmol). The mixture was heated to 110° C. for 3 h. The mixture was purified by flash chromatography to give the title compound of step C (0.29 g, 1.06 mmol, 95%). 1H NMR (400 MHz, CDCl3) δ ppm 7.79 (d, J=8.42 Hz, 1H), 7.11 (d, J=1.47 Hz, 1H), 7.06 (dd, J=8.33, 1.56 Hz, 1H), 3.94 (s, 3H), 3.50 (s, 2H), 2.54-2.63 (m, 4H), 1.62-1.70 (m, 4H), 1.41-1.50 (m, 2H).

Workup

customThe mixture was purified by flash chromatography

Sources & evidence

ORD record: ord-25fe9085c4744a05ae986f59fbf4ac23
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093239B2

Reaction notes

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