3-Aminopiperidine-2,6-dione hydrochloride → HCID 58827304, compound

HRID 448319Notes

Reaction equation

HRID 448319 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[CH:20]=[CH:19][CH:18]=[C:14]([C:15]([OH:17])=O)[C:13]=2[C:21]([OH:23])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].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:28]=[C:27]1[CH:26]([N:25]2[C:21](=[O:23])[C:13]3[C:14](=[CH:18][CH:19]=[CH:20][C:12]=3[NH:11][C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[C:15]2=[O:17])[CH2:32][CH2:31][C:30](=[O:33])[NH:29]1

Participants

4

Reactant 2

HCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 58307134HCID 58307134, compound

Product 1

HCID 58827304HCID 58827304, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-(3,4-dimethoxyphenylamino)phthalic acid (0.59 g, 1.9 mmol) and rac-α-aminoglutarimide hydrochloride (0.32 g, 1.9 mmol) in pyridine (10 mL) was heated to reflux for 16 hours. The mixture was cooled and evaporated under vacuum. The residue was chromatographed using a methylene chloride-methanol gradient, eluting 0.64 g of the product at 96:4 methylene chloride-methanol, in 85% yield: mp>215-217° C.; 1H NMR (CDCl3) δ 2.15-2.19 (m, 1H), 2.74-2.96 (m, 3H), 3.88 (s, 3H), 3.91 (s, 3H), 4.97 (dd, J=11.8 Hz, J=5.1 Hz, 1H), 6.78-6.81 (m, 1H), 6.85-6.91 (m, 2H), 7.16-7.21 (m, 2H), 7.45 (t, J=7.8 Hz, 1H), 7.87 (s, 1H), 8.07 (s, 1H); 13C NMR (CDCl3) δ 22.8, 31.4, 49.0, 56.0, 56.2, 108.6, 110.9, 111.8, 113.2, 116.5, 118.5, 131.7, 132.4, 135.9, 145.2, 147.1, 149.8, 167.4, 168.2, 169.4, 170.8; Anal. calcd for C21H19N3O6: C, 61.61; H, 4.68; N, 10.26. Found: C, 61.47; H, 4.52; N, 10.12.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours
  3. temperatureThe mixture was cooled
  4. customevaporated under vacuum
  5. customThe residue was chromatographed
  6. washeluting 0.64 g of the product at 96:4 methylene chloride-methanol

Sources & evidence

ORD record
ord-8dc6dae1a7d14964b7907b07ac9ef135
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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