3-Aminopiperidine-2,6-dione hydrochloride → HCID 25015053, compound

HRID 1690453Notes

Reaction equation

HRID 1690453 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[CH2:6][O:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:10]([C:11]([OH:13])=O)[C:9]=1[C:17]([OH:19])=O.Cl.[NH2:24][CH:25]1[CH2:31][CH2:30][C:29](=[O:32])[NH:28][C:26]1=[O:27]>N1C=CC=CC=1>[O:27]=[C:26]1[CH:25]([N:24]2[C:17](=[O:19])[C:9]3[C:10](=[CH:14][CH:15]=[CH:16][C:8]=3[O:7][CH2:6][C:5]3[CH:20]=[CH:21][CH:22]=[C:3]([O:2][CH3:1])[CH:4]=3)[C:11]2=[O:13])[CH2:31][CH2:30][C:29](=[O:32])[NH:28]1

Participants

4

Reactant 2

HCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 669063963-(3-Methoxy-benzyloxy)-phthalic acid

Product 1

HCID 25015053HCID 25015053, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-(3-methoxy-benzyloxy)-phthalic acid (1.5 g, 5.2 mmol), alpha-amino-glutarimide hydrochloride (0.89 g, 5.4 mmol) in pyridine was refluxed overnight. The mixture was evaporated and the residue was purified by flash column chromatography (methanol/methylene chloride) to give 2-(2,6-dioxo-piperidin-3-yl)-4-(3-methoxy-benzyloxy)-isoindole-1,3-dione as a white solid (0.25 g, 12% yield); HPLC: Waters Symmetry C18, 5 μm, 3.9×150 mm, 1 mL/min, 240 nm, 60/40 CH3CN/0.1% H3PO4, 2.41 min (99.1%); mp, 197-201° C.; 1H NMR (DMSO-d6) δ 2.02-2.06 (m, 1H, CHH), 2.59-2.62 (m, 2H, CH2), 2.83-2.90 (m, 1H, CHH), 3.77 (s, 3H, CH3), 5.10 (dd, J=6, 12 Hz, 1H, CH), 5.35 (s, 2H, CH2), 6.89-7.85 (m, 7H, Ar), 11.11 (s, 1H, NH); 13C NMR (DMSO-d6) δ 21.95, 30.92, 48.75, 55.01, 69.80, 112.72, 113.27, 115.55, 116.66, 119.17, 120.21, 129.61, 133.25, 136.98, 137.74, 155.42, 159.35, 165.32, 166.77, 169.90, 172.74. Anal Calcd For C21H18N2O6+0.1H2O: C, 63.67; H, 4.63; N, 7.07. Found: C, 63.49; H, 4.40; N, 7.00.

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-b7fa0240588541caa7ad2d3823ad1d44
Source dataset
uspto-grants-2012_04
Patent number
US08153659B2

Reaction notes

Loading…