Piperazine → N,2,6-Trimethyl-4-piperazin-1-yl-pyridine-3-carboxamide

HRID 333965Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH3:9])[C:3]=1[C:10]([NH:12][CH3:13])=[O:11].[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>N1C=CC=CC=1>[CH3:13][NH:12][C:10]([C:3]1[C:4]([CH3:9])=[N:5][C:6]([CH3:8])=[CH:7][C:2]=1[N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)=[O:11]

Participants

Conditions

Temperature: 180 °C

Procedure

4-Chloro-N,2,6-trimethyl-pyridine-3-carboxamide (300 mg, 1.5 mmol) was mixed with piperazine (645 mg, 7.5 mmol) and pyridine (3 ml) and heated under microwave irridation at 180° C. for 15 minutes. The solvent was removed under reduced pressure, the residue was taken up in 0.5 M NaOH saturated with sodium chloride and extracted with dichloromethane (2×). The combined extracts were dried over sodium sulfate, the solvent was evaporated under reduced pressure to yield 280 mg of a yellow solid (1.1 mmol, 75%). NMR (1H, 300 MHz, CD3CN): 6.73 (s, 1H), 6.70 (s, 1H), 2.99-3.02 (m, 4H), 2.82-2.86 (m, 7H), 2.37 (s, 3H), 2.35 (s, 3H).

Workup

customThe solvent was removed under reduced pressure
extractionextracted with dichloromethane (2×)
dry with materialThe combined extracts were dried over sodium sulfate
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-8fa8229a15ee41458b82f5b0ec57cb41
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883791B2

Reaction notes

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