3-Amino-3-methylpiperidine-2,6-dione hydrochloride → HCID 67230396, compound

HRID 448416Notes

Reaction equation

HRID 448416 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:12]([C:13]([OH:15])=O)[C:11]=1[C:19]([OH:21])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:23][C:24]1([CH3:32])[CH2:29][CH2:28][C:27](=[O:30])[NH:26][C:25]1=[O:31]>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:12]2[C:11]=1[C:19](=[O:21])[N:23]([C:24]1([CH3:32])[CH2:29][CH2:28][C:27](=[O:30])[NH:26][C:25]1=[O:31])[C:13]2=[O:15])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 219282523-Amino-3-methylpiperidine-2,6-dione hydrochlorideHCID 67230375HCID 67230375, compound

Product 1

HCID 67230396HCID 67230396, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-(t-butoxycarbonylamino-methyl)-phthalic acid (3.3 g, 11.2 mmol) and 3-amino-3-methyl-piperidine-2,6-dione hydrochloride (2.0 g, 11.2 mmol) in pyridine (40 mL) was refluxed for 17 hours. The mixture was cooled and concentrated. The residue was dissolved in EtOAc (200 mL) and water (50 mL). The organic layer was washed with water (40 mL), Sat. NaHCO3 (40 mL), water (40 mL), and brine (40 mL), and dried (MgSO4). Solvent was removed, and the residue was purified by chromatography (Silica gel) to give [2-(3-methyl-2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-carbamic acid t-butyl ester (2.3 g, 51%): 1H NMR (CDCl3) δ 1.43 (s, 9H, 3(CH3)), 2.08 (s, 3H, CH3), 2.10-2.15 (m, 1H), 2.69-2.84 (m, 3H), 4.62 (d, J=6.5 Hz, 2H, CH2), 5.46 (m, 1H, NH), 7.64-7.76 (m, 3H, Ar), 8.15 (s, 1H, NH).

Workup

  1. temperaturewas refluxed for 17 hours
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in EtOAc (200 mL)
  5. washThe organic layer was washed with water (40 mL), Sat. NaHCO3 (40 mL), water (40 mL), and brine (40 mL)
  6. dry with materialdried (MgSO4)
  7. customSolvent was removed
  8. customthe residue was purified by chromatography (Silica gel)

Sources & evidence

ORD record
ord-d63464dd3e5c4446a4a87557b0ed7742
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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