Potassium Carbonate → 3-methyl-2-{4-[3-(1-piperidinyl)propoxy]phenyl}-1(2H)-isoquinolinone

HRID 2386952Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]([CH3:18])=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:19])=[CH:4][CH:3]=1.Br.Br[CH2:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:18][C:17]1[N:8]([C:5]2[CH:6]=[CH:7][C:2]([O:1][CH2:22][CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:3][CH:4]=2)[C:9](=[O:19])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

Conditions

Temperature: 80 °C

Procedure

2-(4-hydroxyphenyl)-3-methyl-1(2H)-isoquinolinone (30 mg, 0.12 mmol), 1-(3-bromopropyl)piperidine hydrobromide (51 mg, 0.18 mmol) and potassium carbonate (49 mg, 0.36 mmol) were mixed in dimethylformamide (3 mL) and stirred at 80° C. for 3 hours. The solvent was distilled off under reduced pressure, distilled water was added. and the mixture extracted with ethyl acetate. The organic phase was dried with anhydrous sodium sulfate, and the product purified by silica gel column chromatography (chloroform/methanol=20/1) to obtain the title compound (18 mg, 40%) as a colorless solid.

Workup

distillationThe solvent was distilled off under reduced pressure
distillationdistilled water
additionwas added
extractionand the mixture extracted with ethyl acetate
dry with materialThe organic phase was dried with anhydrous sodium sulfate
customthe product purified by silica gel column chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record: ord-4ead1654c0d74347bd8974373ea00ae3
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268842B2

Reaction notes

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