3-Aminopiperidine-2,6-dione hydrochloride → HCID 58827336, compound

HRID 448350Notes

Reaction equation

HRID 448350 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[CH:22]=[CH:21][CH:20]=[C:16]([C:17](O)=[O:18])[C:15]=3[C:23](O)=[O:24])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:27][CH:28]1[CH2:34][CH2:33][C:32](=[O:35])[NH:31][C:29]1=[O:30]>N1C=CC=CC=1>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:14]3[CH:22]=[CH:21][CH:20]=[C:16]4[C:15]=3[C:23](=[O:24])[N:27]([CH:28]3[CH2:34][CH2:33][C:32](=[O:35])[NH:31][C:29]3=[O:30])[C:17]4=[O:18])=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 58307243HCID 58307243, compound

Product 1

HCID 58827336HCID 58827336, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-(4-cyclohexylphenylamino)phthalic acid (0.80 g, 2.4 mmol) and rac-α-aminoglutarimide hydrochloride (0.39 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 in 1:1 hexanes-ethyl acetate, eluting 0.86 g of the product, in 86% yield: mp 219-221° C.; 1H NMR (DMSO-d6) δ 1.10-1.46 (m, 5H), 1.67-1.80 (m, 5H), 2.04-2.07 (m, 1H), 2.40-2.50 (m, 1H), 2.53-2.64 (m, 2H), 2.83-2.90 (m, 1H), 5.12 (dd, J=12.6 Hz, J=5.3 Hz, 1H), 7.19-7.24 (m, 5H), 7.35 (d, J=8.6 Hz, 1H), 7.58 (t, J=7.9 Hz, 1H), 8.34 (s, 1H), 11.14 (s, 1H); 13C NMR (DMSO-d6) δ 22.1, 25.6, 26.4, 31.0, 34.0, 43.2, 48.7, 111.3, 113.0, 119.0, 122.4, 127.6, 132.4, 136.2, 136.9, 143.3, 143.7, 167.1, 168.4, 170.0, 172.8; Anal. calcd for C25H25N3O4: C, 69.59; H, 5.84; N, 9.74. Found: C, 69.38; H, 5.85; N, 9.41.

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 0.86 g of the product

Sources & evidence

ORD record
ord-7b4c4b0d2ff24de5b616cf8b2ebafc08
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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