tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-(di(pyridin-3-yl)methyl)piperazine-1-carboxylate

HRID 2278171Notes

Reaction equation

Cl[CH:2]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.[N:15]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>C(#N)C>[N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH:2]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[N:18]2[CH2:17][CH2:16][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19]2)[CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A round bottom flask was charged with 3,3′-(chloromethylene)-dipyridine (415 mg, 2.03 mmol), tert-butyl piperazine-1-carboxylate (1.20 g, 6.45 mmol), and acetonitrile (50 mL). The reaction was heated to 80° C. for 2 hrs, concentrated under reduced pressure, and purified by silica chromatography (100% CH2Cl2 to 5% 2M NH3 in MeOH) yielding tert-butyl 4-(di(pyridin-3-yl)methyl)piperazine-1-carboxylate (220 mg, 31%). 1H NMR 400 MHz (CDCl3) δ 8.64 (d, J=2.0 Hz, 3H), 8.48 (dd, J=4.8, 1.7 Hz, 3H), 7.70 (dt, J=7.9, 1.9 Hz, 3H), 7.24 (ddd, J=7.9, 4.8, 0.7 Hz, 3H), 5.28 (s, 1H), 4.36 (s, 1H), 3.47-3.39 (m, 6H), 2.34 (s, 6H), 1.42 (s, 9H). LCMS (ESI, m/z): 355 [M+H]+.

Workup

concentrationconcentrated under reduced pressure
custompurified by silica chromatography (100% CH2Cl2 to 5% 2M NH3 in MeOH)

Sources & evidence

ORD record: ord-40993318998a45eda7b46cb64bec36a6
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133148B2

Reaction notes

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