3-Aminopiperidine-2,6-dione hydrochloride → HCID 58827324, compound

HRID 448334Notes

Reaction equation

HRID 448334 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:18]=[CH:17][CH:16]=[C:12]([C:13]([OH:15])=O)[C:11]=2[C:19]([OH:21])=O)=[CH:5][CH:4]=1.Cl.[NH2:23][CH:24]1[CH2:30][CH2:29][C:28](=[O:31])[NH:27][C:25]1=[O:26]>N1C=CC=CC=1>[O:26]=[C:25]1[CH:24]([N:23]2[C:19](=[O:21])[C:11]3[C:12](=[CH:16][CH:17]=[CH:18][C:10]=3[NH:9][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[C:13]2=[O:15])[CH2:30][CH2:29][C:28](=[O:31])[NH:27]1

Participants

4

Reactant 2

HCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 58307149HCID 58307149, compound

Product 1

HCID 58827324HCID 58827324, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-(4-methoxyphenylamino)phthalic acid (0.52 g, 1.8 mmol) and rac-α-aminoglutarimide hydrochloride (0.30 g, 1.8 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 in 95:5 methylene chloride-methanol, eluting 0.58 g of the product, in 84% yield: mp 228-230° C.; 1H NMR (DMSO-d6) δ 2.04-2.09 (m, 1H), 2.52-2.64 (m, 2H), 2.83-2.96 (m, 1H), 3.77 (s, 3H), 5.12 (dd, J=12.6 Hz, J=5.4 Hz, 1H), 6.96-7.00 (m, 2H), 7.12-7.17 (m, 2H), 7.24-7.28 (m, 2H), 7.54 (t, J=7.9 Hz, 1H), 8.24 (s, 1H), 11.13 (s, 1H); 13C NMR (DMSO-d6) δ 22.1, 31.0, 48.7, 55.3, 110.6, 112.4, 114.7, 118.5, 125.3, 131.8, 132.4, 136.1, 144.3, 156.6, 167.1, 168.4, 170.0, 172.8; Anal. calcd for C20H17N3O5: C, 63.32; H, 4.52; N, 11.08. Found: C, 63.31; H, 4.47; N, 10.83.

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 in 95:5 methylene chloride-methanol
  9. washeluting 0.58 g of the product

Sources & evidence

ORD record
ord-af727dac91554c0a9ecc6a71436db4d2
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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