Hydrochloric Acid → HCID 69049940, compound

HRID 331557Notes

Reaction equation

HRID 331557 reaction equation
[CH3:1][C:2]1([N:10]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:19]#[N:20])[CH:16]=3)[C:11]2=[O:21])[CH2:7][CH2:6][C:5](=[O:8])[NH:4][C:3]1=[O:9].[ClH:22]>CC(O)C.O.O=[Pt]=O>[ClH:22].[NH2:20][CH2:19][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:21])[N:10]([C:2]1([CH3:1])[CH2:7][CH2:6][C:5](=[O:8])[NH:4][C:3]1=[O:9])[CH2:18]2

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 670233462-(3-methyl-2,6-dioxo-piperidin-3-yl)-1-oxo-2,3-dihydro-1H-isoindole-5-carbonitrile

Product 1

HCID 69049940HCID 69049940, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 2-(3-methyl-2,6-dioxo-piperidin-3-yl)-1-oxo-2,3-dihydro-1H-isoindole-5-carbonitrile (1.20 g, 4.00 mmol) and PtO2 (0.4 g) in 5-6 N HCl in iPrOH was hydrogenated (55 psi, rt) for 24 h. The resulting mixture was diluted with water (30 mL) and filtered through celite. The celite was washed with water (30 mL) and the combined filtrates were concentrated in vacuo. The residue was triturated in acetonitrile (50 mL) and the product was isolated by filtration and dried in vacuo providing 3-(5-aminomethyl-1-oxo-1,3-dihydro-isoindol-2-yl)-3-methyl-piperidine-2,6-dione hydrochloride (1.2 g, 92% yield); 1H NMR (DMSO-d6) δ 1.70 (s, 3H), 1.87-1.93 (m, 1H), 2.55-2.82 (m, 3H), 4.14 (s, 2H), 4.66 (d, J=17.7 Hz, 1H), 4.75 (d, J=17.7 Hz, 1H), 7.61-7.74 (m, 3H), 8.60 (br, 3H), 10.88 (s, 1H).

Workup

  1. custom(55 psi, rt)
  2. customfor 24 h
  3. filtrationfiltered through celite
  4. washThe celite was washed with water (30 mL)
  5. concentrationthe combined filtrates were concentrated in vacuo
  6. customThe residue was triturated in acetonitrile (50 mL)
  7. customthe product was isolated by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-a65cc78f5e814ac8ad78c210f60c16e2
Source dataset
uspto-grants-2014_11
Patent number
US08877780B2

Reaction notes

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