4-Cyanobenzaldehyde → HCID 67130691, compound

HRID 2380964Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[C:22]([C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1)#[N:23].[BH4-].[Na+]>O1CCCC1>[C:16]1([N:13]2[CH2:14][CH2:15][N:10]([C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][CH2:28][C:27]4[CH:30]=[CH:31][C:24]([C:22]#[N:23])=[CH:25][CH:26]=4)=[CH:7][CH:6]=3)=[O:9])[CH2:11][CH2:12]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of (4-amino-phenyl)-(4-phenyl-piperazin-1-yl)-methanone (0.5 g, 1.78 mmol) in tetrahydrofuran (10 mL) was added 4-cyanobenzaldehyde (0.4 g, 2.67 mmol) followed by sodium borohydride and the reaction was heated to 50° C. for 2 hours. On cooling, the reaction was quenched by the addition of water (10 mL) and the aqueous solution basified by the addition of ammonium chloride (˜pH 8). The aqueous mixture was extracted using dichloromethane (3×10 ml) and the organic extracts combined, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as an off white solid (604 mg, 98% yield). HPLC retention time 7.17 min. Mass spectrum (ES+) m/z 397 (M+H).

Workup

temperatureOn cooling
customthe reaction was quenched by the addition of water (10 mL)
additionthe aqueous solution basified by the addition of ammonium chloride (˜pH 8)
extractionThe aqueous mixture was extracted
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9606026e63184e11923a209257b8e1db
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258138B2

Reaction notes

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