Morpholine → HCID 23156770, compound

HRID 1098296Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

0.042 ml (0.47 mmol) of morpholine was added to a DMF solution containing 50 mg (0.16 mmol) of the 2-chloro-N-(1-oxo-3-phenyl-1,2-dihydroisoquinolin-7-yl)acetamide obtained in Example 57, and the obtained mixture was then stirred at 100° C. for 30 minutes. Thereafter, 30 ml of a 1 N sodium hydroxide aqueous solution was added to the reaction solution, and the mixture was then extracted with ethyl acetate (50 ml×2). The extract was washed with 30 ml of water, and was then dried over anhydrous magnesium sulfate. Thereafter, the solvent was distilled away under reduced pressure. The precipitated solid was collected by filtration, and the filtrate was then washed with a suitable amount of ether and hexane, so as to obtain 44 mg (76%) of 2-morpholin-4-yl-N-(1-oxo-3-phenyl-1,2-dihydroisoquinolin-7-yl)acetamide in the form of a colorless solid.

Workup

extractionthe mixture was then extracted with ethyl acetate (50 ml×2)
washThe extract was washed with 30 ml of water
dry with materialwas then dried over anhydrous magnesium sulfate
distillationThereafter, the solvent was distilled away under reduced pressure
filtrationThe precipitated solid was collected by filtration
washthe filtrate was then washed with a suitable amount of ether and hexane

Sources & evidence

ORD record: ord-7a87c6e91122469f8a3a424b61a44007
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143274B2

Reaction notes

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