3-Aminopiperidine-2,6-dione hydrochloride → HCID 25015216, compound

HRID 1915182Notes

Reaction equation

HRID 1915182 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][O:8][C:9]2[CH:17]=[CH:16][CH:15]=[C:11]([C:12]([OH:14])=O)[C:10]=2[C:18]([OH:20])=O)=[CH:5][CH:4]=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:18](=[O:20])[C:10]3[C:11](=[CH:15][CH:16]=[CH:17][C:9]=3[O:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:22][CH:21]=3)[C:12]2=[O:14])[CH2:31][CH2:30][C:29](=[O:32])[NH:28]1

Participants

4

Reactant 2

HCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 66906835HCID 66906835, compound

Product 1

HCID 25015216HCID 25015216, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A stirred mixture of 3-(4-methoxy-benzyloxy)-phthalic acid (1.5 g, 5.2 mmol), alpha-amino-glutarimide hydrochloride (0.90 g, 5.4 mmol) in pyridine was refluxed overnight. The mixture was evaporated in vacuo, and the residue was purified by flash column chromatography (Silica Gel, methanol/methylene chloride, 0% gradient to 10% 30 min) to give 2-(2,6-dioxo-piperidin-3-yl)-4-(4-methoxy-benzyloxy)-isoindole-1,3-dione as a white solid (0.83 g, 40% yield); HPLC: Waters Symmetry C18, 5 μm, 3.9×150 mm, 1 mL/min, 240 nm, 50/50 CH3CN/0.1% H3PO4, RT=4.17 min (98.6%); mp, 178-180° C.; 1HNMR (DMSO-d6) δ1.99-2.06 (m, 1H, CHH), 2.51-2.82 (m, 2H, CHHCH2), 3.76 (s, 3H, CH3), 5.08 (dd, J=6, 12 Hz, 1H, CH), 5.29 (s, 2H, CH2), 6.95-7.84 (m, 7H, Ar), 11.11 (s, 1H, NH); 13C NMR (DMSO-d6) δ 21.96, 30.91, 48.72, 55.08, 69.92, 113.88, 115.41, 116.55, 120.29, 127.93, 129.21, 133.25, 136.92, 155.57, 159.10, 165.28, 166.77, 169.90, 172.75. Anal Calcd For C21H18N2O6: C, 63.96; H, 4.60; N, 7.10. Found: C, 63.86; H, 4.30; N, 6.92.

Workup

  1. temperaturewas refluxed overnight
  2. customThe mixture was evaporated in vacuo
  3. customthe residue was purified by flash column chromatography (Silica Gel, methanol/methylene chloride, 0% gradient to 10% 30 min)

Sources & evidence

ORD record
ord-2e085c2341b943fb865ea4127d748c1b
Source dataset
uspto-grants-2013_12
Patent number
US08614328B2

Reaction notes

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