Phthalimidine → HCID 57949754, compound

HRID 2427571Notes

Reaction equation

HRID 2427571 reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.Br[CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O.CCCCCC.C(OCC)(=O)C>[C:15]1([CH2:14][CH2:13][CH2:12][N:2]2[CH2:3][C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:1]2=[O:10])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 10199PhthalimidineHCID 10796Cesium carbonateHCID 12503(3-Bromopropyl)benzeneHCID 2855718-Crown-6

Product 1

HCID 57949754HCID 57949754, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2,3-dihydro-isoindol-1-one (0.066 g, 0.5 mmol), 3-bromo-propyl-benzene (0.119 g, 0.6 mmol), Cs2CO3 (0.408 g, 1.25 mmol), and 18-crown-6 (0.013 g, 0.05 mmol) in acetone (3 mL) was stirred at 70° C. for 16 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 2-(3-phenyl-propyl)-2,3-dihydro-isoindol-1-one (0.100 g, 80%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.99 (m, 2H), 2.66 (t, 2H), 3.68 (t, 2H), 4.38 (s, 2H), 7.18-7.56 (m, 8H), 7.92 (d, 1H).

Sources & evidence

ORD record
ord-7ed87c6a4c434de29af5502052683833
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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