1-Isopropylpiperazine → 1-[6-(1,3-Dioxolan-2-yl)pyridin-2-yl]-4-isopropylpiperazine

HRID 922392Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-bromo-6-(1,3-dioxolan-2-yl)pyridine (7, 0.23 g, 1.0 mmol) and 1-isopropylpiperazine (0.38 g, 3.0 mmol) in a sealed tube was heated at 120° C. for 18 h. The mixture was cooled to room temperature, diluted with ethyl acetate (50 mL), washed with water (10 mL), brine (10 mL), dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography eluting with 0-10% methanol in dichloromethane to afford the title compound (0.15 g, 55%) as a yellow oil: 1H NMR (500 MHz, CDCl3) δ 7.51-7.48 (m, 1H), 6.83-6.82 (m, 1H), 6.62-6.60 (m, 1H), 5.72 (s, 1H), 4.18-4.14 (m, 2H), 4.08-4.04 (m, 2H), 3.58 (br s, 4H), 2.71 (br s, 1H), 2.62 (br s, 2H), 1.08 (d, J=5.5 Hz, 6H); ESI MS m/z 278 [M+H]+.

Workup

temperatureThe mixture was cooled to room temperature
washwashed with water (10 mL), brine (10 mL)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel chromatography
washeluting with 0-10% methanol in dichloromethane

Sources & evidence

ORD record: ord-9c9cbe803b03453dab40db7e6f392dc9
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278940B2

Reaction notes

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