Diethylaminoethyl chloride → HCID 21487244, compound

HRID 1414384Notes

Reaction equation

[OH:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+].Cl[CH2:21][CH2:22][N:23]([CH2:26][CH3:27])[CH2:24][CH3:25]>>[CH2:22]([N:23]([CH2:26][CH3:27])[CH2:24][CH2:25][O:11][CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:21]

Participants

Reactant 3

HCID 13364Diethylaminoethyl chloride

HCID 24758Sodium hydride

HCID 866702,3-Dihydro-3-hydroxy-2-phenyl-1H-isoindol-1-one

Product 1

HCID 21487244HCID 21487244, compoundYield 105.3%

Procedure

Following the procedure of Example 6 but starting with 3-hydroxy-2-phenyl-isoindolin-1-one (22.5 g.), sodium hydride (50% dispersion in mineral oil) (5.3 g.) and 1-chloro-2-diethylaminoethane (13.5 g.), 3-(2-diethylaminoethoxy)-2-phenyl-isoindolin-1-one (34 g.) is obtained in the form of an 85% pure oil. On treating this oil (28 g.) with fumaric acid (8.5 g.) in ethanol, 3-(2-diethylaminoethoxy)-2-phenyl-isoindolin-1-one hydrogen fumarate (27.6 g.), which melts at 146°-147°C., is obtained.

Sources & evidence

ORD record: ord-3908ffd8915f4ba4ac130d0a9f6d8781
Source dataset: uspto-grants-1977_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04001271

Reaction notes

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