Phthalimide → (5)-2-(1-(4-(Methoxy)phenyl)ethyl)isoindoline-1,3-dione

HRID 709434

Reaction equation

[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20](N)[CH3:21])=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CCCCO>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]([N:5]2[C:1](=[O:11])[C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]2=[O:6])[CH3:21])=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 160 °C

Procedure

To phthalimide (1.3 g, 0.0088 mol) in a 2-5 mL microwave vial was added (S)-1-(4-methoxyphenyl)ethan-1-amine (2.20 mL, 0.015 mol) and K2CO3 (1.2 g, 0.0087 mol). The reaction mixture capped and heated at 160° C. for 2 minutes. The resulting crude solid was suspended in n-BuOH and was filtered. The filtrate was put aside. The solid was washed with H2O and the filtrate was discarded. The solid was washed with CH2Cl2 and the resulting filtrate was partitioned with H2O. The organics (n-BuOH and CH2Cl2 layer) were combined and concentrated. The crude residue was purified by silica gel column chromatography using CH2Cl2 as eluent to yield 1.6 g (64%) of the title compound. LC/MS: m/z (ES+) 282 (M+H)+.

Workup

customThe reaction mixture capped
filtrationwas filtered
washThe solid was washed with H2O
washThe solid was washed with CH2Cl2
customthe resulting filtrate was partitioned with H2O
concentrationconcentrated
customThe crude residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-c18f34cedcee43ec9062a99d9d271c44
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181200B2

Linked notes

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