3-Aminopiperidine-2,6-dione hydrochloride → HCID 58827277, compound

HRID 448313Notes

Reaction equation

HRID 448313 reaction equation
[C:1]1([NH:7][C:8]2[CH:16]=[CH:15][CH:14]=[C:10]([C:11]([OH:13])=O)[C:9]=2[C:17]([OH:19])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:21][CH:22]1[CH2:28][CH2:27][C:26](=[O:29])[NH:25][C:23]1=[O:24]>N1C=CC=CC=1>[O:24]=[C:23]1[CH:22]([N:21]2[C:17](=[O:19])[C:9]3[C:10](=[CH:14][CH:15]=[CH:16][C:8]=3[NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:11]2=[O:13])[CH2:28][CH2:27][C:26](=[O:29])[NH:25]1

Participants

4

Reactant 2

HCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 20130021HCID 20130021, compound

Product 1

HCID 58827277HCID 58827277, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-phenylaminophthalic acid (0.52 g, 2.0 mmol) and rac-α-aminoglutarimide hydrochloride (0.33 g, 2.0 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 hexanes-ethyl acetate gradient, eluting 0.60 g of the product at 4:6 hexanes-ethyl acetate, in 83% yield: mp 214-216° C.; 1H NMR (DMSO-d6) δ 1.99-2.09 (m, 1H), 2.53-2.64 (m, 2H), 2.84-2.97 (m, 1H), 5.13 (dd, J=12.6 Hz, J=5.4 Hz, 1H), 7.11-7.16 (m, 1H), 7.25 (d, J=7.0 Hz, 1H), 7.31-7.45 (m, 5H), 7.61 (t, J=7.8 Hz, 1H), 8.45 (s, 1H), 11.14 (s, 1H); 13C NMR (DMSO-d6) δ 22.1, 31.0, 48.7, 112.0, 113.4, 119.4, 121.9, 124.0, 129.4, 132.5, 136.2, 139.4, 142.8, 167.0, 168.3, 170.0, 172.8; Anal. calcd for C19H15N3O4: C, 65.32; H, 4.33; N, 12.03. Found: C, 64.93; H, 4.33; N, 11.79.

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 0.60 g of the product at 4:6 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-ca3ccda9c9cc41e79e37d2771cdd8f0a
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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