Potassium Carbonate → 4-(4-Benzylpiperazin-1-yl)benzonitrile

HRID 131140Notes

Reaction equation

F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH2:10]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:10]([N:17]1[CH2:22][CH2:21][N:20]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH2:19][CH2:18]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 4-fluorobenzonitrile (3.0 g, 25 mmol) in N,N-dimethylformamide (15 mL) were added 1-benzylpiperazine (4.3 mL, 25 mmol) and potassium carbonate (3.4 g, 25 mmol). The reaction mixture was stirred at 120° C. for 13 h. The solvent was evaporated in vacuo and the residue was partitioned between ethyl acetate (100 mL) and water (15 mL). The aqueous phase was extracted with ethyl acetate (30 mL) and the combined organic phases were washed twice with brine (10 mL) and dried (MgSO4). Evaporation of the solvent gave 7.6 g of crude product. Purification of the residue on a silica gel column using ethyl acetate/methylene chloride (1:9) as the eluent afforded 4.0 g (59% yield) of the title compound as a white solid: mp 104-105° C.; EIMS (70 eV) m/z (relative intensity) 277 (20, M+).

Workup

customThe solvent was evaporated in vacuo
customthe residue was partitioned between ethyl acetate (100 mL) and water (15 mL)
extractionThe aqueous phase was extracted with ethyl acetate (30 mL)
washthe combined organic phases were washed twice with brine (10 mL)
dry with materialdried (MgSO4)
customEvaporation of the solvent
customgave 7.6 g of crude product
customPurification of the residue on a silica gel column

Sources & evidence

ORD record: ord-aca30f9d8f5c46b8af40642872c3f795
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384943B2

Reaction notes

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