Water → HCID 59323472, compound

HRID 2390055Notes

Reaction equation

[CH2:1]([CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][N:9]1[CH2:18][CH2:19][NH2:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=1)#[N:22].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[C:21]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH:20][CH2:19][CH2:18][N:9]2[CH:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10]2)=[CH:25][CH:24]=1)#[N:22]

Participants

Conditions

Temperature: 60 °C

Procedure

2-[3-benzyl-3,4-dihydroisoquinolin-2(1H)-yl]ethanamine (27 mg, 0.1 mmol) obtained in Example 1-f), 4-cyanobenzylbromide (20 mg, 0.1 mmol), and potassium carbonate (17 mg, 0.12 mmol) were dissolved in 1 mL of acetonitrile, followed by stirring at 60° C. for 3 hours. After completion of the reaction, water was added to the reaction liquid, followed by extraction with ethyl acetate, and the organic layer was then washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue obtained was purified using silica gel chromatography (chloroform:methanol=10:1) to obtain 14 mg (yield 36.7%) of a title compound as a colorless oily substance.

Workup

additionwas added to the reaction liquid
extractionfollowed by extraction with ethyl acetate
washthe organic layer was then washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue obtained
customwas purified

Sources & evidence

ORD record: ord-5a4c22cca7d84e66887414bd11811fc9
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273766B2

Reaction notes

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