Potassium Carbonate → 4-(4-Pyridin-3-ylmethylpiperazin-1-yl)benzonitrile

HRID 1727253Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:2]=1.F[C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)[CH:2]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 1-(pyridin-3-ylmethyl)piperazine (549 mg, 3.10 mmol), 4-fluorobenzonitrile (375 mg, 3.10 mmol), and K2CO3 (643 mg, 4.65 mmol) in DMF (50 mL) was stirred at 80° C. overnight. The reaction mixture was cooled to room temperature and filtered, and the filtrate was washed with ethyl acetate (30 nL). The combined filtrate and washings were evaporated to dryness under reduced pressure. The crude residue was purified by MPLC on silica gel (3% MeOH in CH2Cl2) to afford the titled compound (326 mg, 38%) as a yellow solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered
washthe filtrate was washed with ethyl acetate (30 nL)
customThe combined filtrate and washings were evaporated to dryness under reduced pressure
customThe crude residue was purified by MPLC on silica gel (3% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-099310aa7fbb4fe2affa6c2380e118cc
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495022B2

Reaction notes

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