3-Aminopiperidine-2,6-dione hydrochloride → HCID 58827240, compound

HRID 448331Notes

Reaction equation

HRID 448331 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[NH:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:14]([C:15]([OH:17])=O)[C:13]=1[C:21]([OH:23])=O.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>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[NH:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:14]2[C:13]=1[C:21](=[O:23])[N:25]([CH:26]1[CH2:32][CH2:31][C:30](=[O:33])[NH:29][C:27]1=[O:28])[C:15]2=[O:17]

Participants

4

Reactant 2

HCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 583073283-(2,4-Dimethoxyphenylamino)phthalic acid

Product 1

HCID 58827240HCID 58827240, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-(2,4-dimethoxyphenylamino)phthalic acid (0.75 g, 2.4 mmol) and rac-α-aminoglutarimide hydrochloride (0.40 g, 2.4 mmol) in pyridine (10 mL) was heated to reflux for 16 hours. The mixture was cooled and evaporated under vacuum. The residue was dissolved in ethyl acetate (150 mL), washed with dilute aqueous HCl (2×100 mL) and water (2×100 mL), and evaporated. The residue was chromatographed using a hexanes-ethyl acetate gradient, eluting 0.64 g of the product at 25:75 hexanes-ethyl acetate, in 67% yield: mp 208-210° C.; 1H NMR (DMSO-d6) δ 2.04-2.09 (m, 1H), 2.54-2.64 (m, 2H), 2.83-2.92 (m, 1H), 3.78 (s, 3H), 3.79 (s, 3H), 5.12 (dd, J=12.7 Hz, J=5.4 Hz, 1H), 6.57 (dd, J=8.6 Hz, J=2.6 Hz, 1H), 6.71 (d, J=2.6 Hz, 1H), 7.00 (d, J=8.6 Hz, 1H), 7.15 (d, J=7.0 Hz, 1H), 7.29 (d, J=8.7 Hz, 1H), 7.54 (t, J=7.9 Hz, 1H), 7.95 (s, 1H), 11.15 (s, 1H); 13C NMR (DMSO-d6) δ 22.1, 31.0, 48.7, 55.4, 55.7, 99.5, 104.7, 110.4, 112.2, 118.3, 120.1, 125.2, 132.1, 136.1, 144.2, 153.7, 157.9, 167.2, 168.9, 170.1, 172.8; Anal. calcd for C21H19N3O6.0.3H2O: C, 60.81; H, 4.76; N, 10.13. Found: C, 60.87; H, 4.64; N, 10.00.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours
  3. temperatureThe mixture was cooled
  4. customevaporated under vacuum
  5. dissolutionThe residue was dissolved in ethyl acetate (150 mL)
  6. washwashed with dilute aqueous HCl (2×100 mL) and water (2×100 mL)
  7. customevaporated
  8. customThe residue was chromatographed
  9. washeluting 0.64 g of the product at 25:75 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-8fee5da970ff4f198c6dafaa8ac2f68f
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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