3-Aminopiperidine-2,6-dione hydrochloride → HCID 58827302, compound

HRID 448327Notes

Reaction equation

HRID 448327 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[CH:19]=[CH:18][CH:17]=[C:13]([C:14]([OH:16])=O)[C:12]=2[C:20](O)=[O:21])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].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>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[CH:19]=[CH:18][CH:17]=[C:13]3[C:12]=2[C:20](=[O:21])[N:24]([CH:25]2[CH2:31][CH2:30][C:29](=[O:32])[NH:28][C:26]2=[O:27])[C:14]3=[O:16])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 58307280HCID 58307280, compound

Product 1

HCID 58827302HCID 58827302, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-(4-isopropylphenylamino)phthalic acid (0.64 g, 2.1 mmol) and rac-α-aminoglutarimide hydrochloride (0.35 g, 2.1 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 1:1 hexanes-ethyl acetate, eluting 0.74 g of the product, in 89% yield: mp 138-140° C.; 1H NMR (DMSO-d6) δ 1.21 (d, J=6.9 Hz, 6H), 2.04-2.08 (m, 1H), 2.52-2.64 (m, 2H), 2.84-2.94 (m, 2H), 5.13 (dd, J=12.6 Hz, J=5.3 Hz, 1H), 7.19-7.30 (m, 5H), 7.35 (d, J=8.5 Hz, 1H), 7.58 (t, J=7.8 Hz, 1H), 8.35 (s, 1H), 11.15 (s, 1H); 13C NMR (DMSO-d6) δ 22.1, 23.9, 31.0, 32.9, 48.7, 111.3, 113.0, 119.0, 122.5, 127.2, 132.4, 136.2, 136.9, 143.3, 144.5, 167.1, 168.4, 170.0, 172.8; Anal. calcd for C22H21N3O4: C, 67.51; H, 5.41; N, 10.74. Found: C, 67.27; H, 5.36; N, 10.64.

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 1:1 hexanes-ethyl acetate
  9. washeluting 0.74 g of the product

Sources & evidence

ORD record
ord-805ace63b4694682b712a942a34492a9
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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