3-Aminopiperidine-2,6-dione hydrochloride → HCID 58827281, compound

HRID 448316Notes

Reaction equation

HRID 448316 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([NH:10][C:11]3[CH:19]=[CH:18][CH:17]=[C:13]([C:14]([OH:16])=O)[C:12]=3[C:20]([OH:22])=O)=[CH:4][C:3]=2[O:2]1.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:20](=[O:22])[C:12]3[C:13](=[CH:17][CH:18]=[CH:19][C:11]=3[NH:10][C:5]3[CH:6]=[CH:7][C:8]4[O:9][CH2:1][O:2][C:3]=4[CH:4]=3)[C:14]2=[O:16])[CH2:31][CH2:30][C:29](=[O:32])[NH:28]1

Participants

4

Reactant 2

HCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 58307299HCID 58307299, compound

Product 1

HCID 58827281HCID 58827281, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-(3,4-methylenedioxyphenylamino)phthalic acid (0.50 g, 1.7 mmol) and rac-α-aminoglutarimide hydrochloride (0.29 g, 1.7 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 0.52 g of the product at 95:5 methylene chloride-methanol, in 80% yield: mp>260° C.; 1H NMR (DMSO-d6) δ 2.03-2.08 (m, 1H), 2.57-2.63 (m, 2H), 2.83-2.96 (m, 1H), 5.11 (dd, J=12.6 Hz, J=5.3 Hz, 1H), 6.04 (s, 2H), 6.80 (dd, J=8.3 Hz, J=1.9 Hz, 1H), 6.92-6.95 (m, 2H), 7.16-7.22 (m, 2H), 7.56 (t, J=7.8 Hz, 1H), 8.25 (s, 1H), 11.12 (s, 1H); 13C NMR (DMSO-d6) δ 22.1, 31.0, 48.7, 101.3, 105.5, 108.6, 110.9, 112.7, 116.7, 118.9, 132.3, 133.2, 136.2, 144.1, 144.5, 147.9, 167.1, 168.3, 170.0, 172.8; Anal. calcd for C20H15N3O6.0.2H2O: C, 60.51; H, 3.91; N, 10.58. Found: C, 60.49; H, 3.62; N, 10.50.

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 0.52 g of the product at 95:5 methylene chloride-methanol

Sources & evidence

ORD record
ord-799456f7991145ebbd40d98d251c7116
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

Loading…