3-Aminopiperidine-2,6-dione hydrochloride → HCID 86709850, compound

HRID 2277130Notes

Reaction equation

HRID 2277130 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:18]=[CH:17][C:16]([OH:19])=[C:11]([C:12]([O:14]C)=O)[C:10]=1[C:20]([O:22]C)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:25][CH:26]1[CH2:31][CH2:30][C:29](=[O:32])[NH:28][C:27]1=[O:33]>N1C=CC=CC=1>[O:33]=[C:27]1[CH:26]([N:25]2[C:20](=[O:22])[C:10]3[C:11](=[C:16]([OH:19])[CH:17]=[CH:18][C:9]=3[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[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 10639746HCID 10639746, compound

Product 1

HCID 86709850HCID 86709850, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of dimethyl 3-(tert-butoxycarbonylamino)-6-hydroxyphthalate C3-3 (7.68 g, 23.6 mmol) and 3-aminopiperidine-2,6-dione hydrochloride (7.77 g, 47.2 mmol) in pyridine (150 mL) was heated at 100° C. overnight. The solvent was removed in vacuo and the residue was purified by chromatography (silica gel, DCM:MeOH:PE) to give compound C3-4 as a yellow solid (6.73 g, yield: 73%). 1H NMR (DMSO-d6, 400 MHz) δ: 1.47 (s, 9H), 1.98-2.02 (m, 1H), 2.54-2.60 (m, 2H), 2.83-2.92 (m, 1H), 5.04 (dd, J=13.0 and 5.4 Hz, 1H), 7.22 (d, J=8.8 Hz, 1H), 8.10 (d, J=9.2 Hz, 1H), 8.68 (s, 1H), 11.01 (s, 1H), 11.11 (s, 1H); MS (ESI+): m/z 412 (M+23).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by chromatography (silica gel, DCM:MeOH:PE)

Sources & evidence

ORD record
ord-dbca1dd5eed04b3285e7aec13a10bcb8
Source dataset
uspto-grants-2015_09
Patent number
US09133161B2

Reaction notes

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