Water → 3-Methyl-4-(piperazin-1-yl)benzonitrile

HRID 1184457Notes

Reaction equation

F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.O>CS(C)=O>[CH3:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[C:6]#[N:7]

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 4-fluoro-3-methylbenzonitrile (2.5 g, 18.50 mmol) in DMSO (10.0 mL) was added piperazine (7.97 g, 92 mmol) at 23° C. The reaction was stirred at 140° C. for 16 hr. The reaction mixture was poured into H2O (100 mL) and the reaction vessel was rinsed with H2O (˜50 mL). The resulting suspension was filtered, rinsed with H2O (3×10 mL) and the resulting solid was dried in vacuo to provide the title compound as a white solid (2.593 g, 12.88 mmol, 69.6% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.21-2.30 (m, 3H) 2.57-2.70 (m, 1H) 2.83 (s, 8H) 7.03-7.09 (m, 1H) 7.55-7.62 (m, 2H). ESI-MS: m/z 202.1 (M+H)+.

Workup

washthe reaction vessel was rinsed with H2O (˜50 mL)
filtrationThe resulting suspension was filtered
washrinsed with H2O (3×10 mL)
customthe resulting solid was dried in vacuo

Sources & evidence

ORD record: ord-72cbb61f61884536b5c931221bcd4c5f
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669249B2

Reaction notes

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