3-Aminopiperidine-2,6-dione hydrochloride → HCID 25015054, compound

HRID 1915161Notes

Reaction equation

HRID 1915161 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][O:11][C:12]3[CH:20]=[CH:19][CH:18]=[C:14]([C:15]([OH:17])=O)[C:13]=3[C:21]([OH:23])=O)=[CH:9][C:4]=2[O:3][CH2:2]1.Cl.[NH2:25][CH:26]1[CH2:32][CH2:31][C:30](=[O:33])[NH:29][C:27]1=[O:28]>N1C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][O:11][C:12]3[CH:20]=[CH:19][CH:18]=[C:14]4[C:13]=3[C:21](=[O:23])[N:25]([CH:26]3[CH2:32][CH2:31][C:30](=[O:33])[NH:29][C:27]3=[O:28])[C:15]4=[O:17])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 66907265HCID 66907265, compound

Product 1

HCID 25015054HCID 25015054, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-(benzo[1,3]dioxol-5-ylmethoxy)-phthalic acid (1.2 g, 3.8 mmol), alpha-amino-glutarimide hydrochloride (0.66 g, 4.0 mmol) in pyridine was refluxed overnight. The mixture was evaporated and the residue was purified by flash column chromatography (methanol/methylene chloride) to give 4-(benzo[1,3]dioxol-5-ylmethoxy)-2-(2,6-dioxo-piperidin-3-yl)-isoindole-1,3-dione as a white solid (0.45 g, 29% yield); HPLC: Waters Symmetry C18, 5 μm, 3.9×150 mm, 1 mL/min, 240 nm, 50/50 CH3CN/0.1% H3PO4, 4.06 min (98.6%); mp, 229-231° C.; 1H NMR (DMSO-d6) δ 2.02-2.05 (m, 1H, CHH), 2.55-2.62 (m, 2H, CH2), 2.82-2.94 (m, 1H, CHH), 5.10 (dd, J=6, 12 Hz, 1H, CH), 5.26 (s, 2H, CH2), 6.03 (s, 2H, CH2), 6.93-7.85 (m, 6H, Ar), 11.11 (s, 1H, NH); 13C NMR (DMSO-d6) δ 21.95, 30.91, 48.74, 70.00, 101.05, 108.10, 108.18, 115.49, 116.61, 120.28, 121.25, 129.78, 133.24, 136.95, 147.04, 147.38, 155.44, 165.30, 166.76, 169.89, 172.74. Anal Calcd For C21H16N2O7: C, 61.77; H, 3.95; N, 6.86. Found: C, 61.44; H, 3.72; N, 6.79.

Workup

  1. temperaturewas refluxed overnight
  2. customThe mixture was evaporated
  3. customthe residue was purified by flash column chromatography (methanol/methylene chloride)

Sources & evidence

ORD record
ord-63e824e5327749f885931779467dfc4b
Source dataset
uspto-grants-2013_12
Patent number
US08614328B2

Reaction notes

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