3-Aminopiperidine-2,6-dione hydrochloride → HCID 9838883, compound

HRID 2185953Notes

Reaction equation

HRID 2185953 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:5]2[C:6]([O:8][C:9](=[O:10])[C:4]=12)=O.Cl.[NH2:15][CH:16]1[CH2:21][CH2:20][C:19](=[O:22])[NH:18][C:17]1=[O:23].C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:5]2[C:4]=1[C:9](=[O:10])[N:15]([CH:16]1[CH2:21][CH2:20][C:19](=[O:22])[NH:18][C:17]1=[O:23])[C:6]2=[O:8]

Participants

5

Reactant 3

HCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 2911934-Methoxy-1,3-dihydro-2-benzofuran-1,3-dioneHCID 517045Sodium Acetate

Product 1

HCID 9838883HCID 9838883, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Methoxy-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione was prepared by the procedure of Example 1 from 3-methoxyphthalic anhydride (1.0 g, 5.6 mmol) {Rao. A. V. R. et al, Indian J. Chem. 1981, 20 (B), 248}, 3-aminopiperidine-2,6-dione hydrogen chloride (0.92 g, 5.6 mmol) and sodium acetate (0.48 g, 6.0 mmol) in acetic acid (20 mL). The product was a white solid (0.44 g, 27% yield); mp, 281.5-282.5° C.; 1H NMR (DMSO-d6) δ2.00-2.08 (m, 1H, CHH), 2.56-2.62 (m, 2H, CH2), 2.82-2.91 (m, 1H, CHH), 3.97 (s, 3H, CH3), 5.08 (dd, J=5.3, 12.8 Hz, 1H, NCH), 7.46 (d, J=7.2 Hz, 1H, Ar), 7.52 (d, J=8.5 Hz, 1H, Ar), 7.84 (d, J=7.8 Hz, 1H, Ar), 11.10 (br s, 1H, NH); 13C NMR (DMSO-d6) δ21.97, 30.92, 48.73, 56.33, 115.24, 116.11, 119.01, 133.19, 137.15, 156.49, 165.37, 166.84, 169.94, 172.79; Anal Calcd for C14H12N2O5: C, 58.33; H, 4.20; N, 9.72. Found: C, 58.23; H, 3.90; N, 9.53.

Sources & evidence

ORD record
ord-4947c65c85aa418c83d1db4656f55279
Source dataset
uspto-grants-2002_06
Patent number
US06403613B1

Reaction notes

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