3-Aminopiperidine-2,6-dione hydrochloride → HCID 25015140, compound

HRID 709583Notes

Reaction equation

HRID 709583 reaction equation
[Cl:1][C:2]1[S:6][C:5]([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:4][CH:3]=1.Cl.[NH2:22][CH:23]1[CH2:29][CH2:28][C:27](=[O:30])[NH:26][C:24]1=[O:25]>N1C=CC=CC=1>[Cl:1][C:2]1[S:6][C:5]([CH2:7][O:8][C:9]2[CH:17]=[CH:16][CH:15]=[C:11]3[C:10]=2[C:18](=[O:20])[N:22]([CH:23]2[CH2:29][CH2:28][C:27](=[O:30])[NH:26][C:24]2=[O:25])[C:12]3=[O:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 669067303-(5-Chloro-thiophen-2-ylmethoxy)-phthalic acid

Product 1

HCID 25015140HCID 25015140, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-(5-chloro-thiophen-2-ylmethoxy)-phthalic acid (1.6 g, 5.1 mmol), alpha-amino-glutarimide hydrochloride (0.88 g, 5.4 mmol) in pyridine was refluxed overnight. The mixture was evaporated and the residue was purified by flash column chromatography (methanol/methylene chloride) to give 4-(5-chloro-thiophen-2-ylmethoxy)-2-(2,6-dioxo-piperidin-3-yl)-isoindole-1,3-dione as a white solid (0.76 g, 36% yield); HPLC: Waters Symmetry C18, 5 μm, 3.9×150 mm, 1 mL/min, 240 nm, 60/40 CH3CN/0.1% H3PO4, 2.63 min (99.3%); mp, 217-219° C.; 1H NMR (DMSO-d6) δ 2.01-2.07 (m, 1H, CHH), 2.54-2.57 (m, 2H, CH2), 2.62-2.95 (m, 1H, CHH), 5.10 (dd, J=6, 12 Hz, 1H, CH), 5.50 (s, 2H, CH2), 7.07-7.87 (m, 5H, Ar), 11.11 (s, 1H, NH); 13C NMR (DMSO-d6) δ 21.93, 30.90, 48.75, 65.38, 115.94, 116.80, 120.44, 126.55, 127.83, 129.09, 133.31, 136.93, 137.54, 154.76, 165.14, 166.68, 169.77, 169.86, 172.73. Anal Calcd For C18H13N2O5SCl: C, 53.41; H, 3.24; N, 6.92; S, 7.92%; Cl, 8.76. Found: C, 53.39; H, 2.95; N, 6.80; S, 7.62%; Cl, 9.01.

Workup

  1. temperaturewas refluxed overnight
  2. customThe mixture was evaporated
  3. customthe residue was purified by flash column chromatography (methanol/methylene chloride)

Sources & evidence

ORD record
ord-58c0a011ba6b4cf4bee691c73074698d
Source dataset
uspto-grants-2015_11
Patent number
US09181216B2

Reaction notes

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