Phenethylamine → N-phenethyl phthalimide

HRID 533357Notes

Reaction equation

HRID 533357 reaction equation
[CH2:1]1[CH:8]([N:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:10]2=[O:11])C(=O)O[C:3](=O)[CH2:2]1.[CH2:20](N)[CH2:21][C:22]1C=CC=C[CH:23]=1>>[CH2:8]([N:9]1[C:10](=[O:11])[C:12]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:17]2[C:18]1=[O:19])[CH2:1][C:2]1[CH:3]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 1001PhenethylamineHCID 921931H-Isoindole-1,3(2H)-dione, 2-(tetrahydro-2,6-dioxo-2H-pyran-3-yl)-

Product 1

HCID 348641N-phenethyl phthalimide

Conditions

Temperature
177 °C

Procedure

With reference to Scheme 3 below, a mixture of N-phthaloyl-DL-glutamic anhydride and phenethylamine was heated in a 177° C. oil bath. The reaction mixture was purified by chromatography on a silica gel column to afford N-phenethylthalidomide (8) and N-phenethylphthalimide (9).

Workup

  1. customThe reaction mixture was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-d6a6d2e2fff44b0b9b08f3c8c04a7aa1
Source dataset
uspto-grants-2014_10
Patent number
US08853253B2

Reaction notes

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