Hydrochloric Acid → 6-(2-Methylpiperazin-1-yl)nicotinonitrile hydrochloride

HRID 874925Notes

Reaction equation

[ClH:1].[C:2]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH:11]2[CH3:23])=[N:8][CH:9]=1)#[N:3]>>[ClH:1].[CH3:23][CH:11]1[CH2:12][NH:13][CH2:14][CH2:15][N:10]1[C:7]1[CH:6]=[CH:5][C:4]([C:2]#[N:3])=[CH:9][N:8]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 69935291Tert-butyl 4-(5-cyanopyridin-2-yl)-3-methylpiperazine-1-carboxylate

Product 1

HCID 673239496-(2-Methylpiperazin-1-yl)nicotinonitrile hydrochloride

Conditions

Temperature: 90 °C

Procedure

6N HCl (1 mL) was added to the compound tert-butyl 4-(5-cyanopyridin-2-yl)-3-methylpiperazine-1-carboxylate (120 mg, 0.39 mmol) and the reaction mixture was stirred at 90° C. for 30 min. The reaction mixture was cooled to room temperature, concentrated under reduced pressure and triturated with ether to afford 6-(2-methylpiperazin-1-yl)nicotinonitrile hydrochloride (90 mg, crude). 1H NMR (400 MHz, D2O) δ 8.39 (d, J=2.0 Hz, 1H), 7.85 (dd, J=9.3 Hz, J=2.3 Hz, 1H), 6.95 (d, J=9.5 Hz, 1H), 4.74 (m, 2H), 4.32-4.27 (m, 1H), 3.48-3.41 (m, 1H), 3.35-3.28 (m, 2H), 3.17-3.10 (m, 1H), 1.27 (d, J=7.0 Hz, 3H)

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated under reduced pressure
customtriturated with ether

Sources & evidence

ORD record: ord-2cd9023be9f444c1911d987bcc2faa92
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08981084B2

Reaction notes

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