Hydrochloric Acid → 3-(4-(Aminomethyl)-1-oxoisoindolin-2-yl)piperidine-2,6-dione hydrochloride

HRID 10064

Reaction equation

HRID 10064 reaction equation
[O:1]=[C:2]1[CH:7]([N:8]2[CH2:16][C:15]3[C:14]([C:17]#[N:18])=[CH:13][CH:12]=[CH:11][C:10]=3[C:9]2=[O:19])[CH2:6][CH2:5][C:4](=[O:20])[NH:3]1.[ClH:21]>CO.[Pd]>[ClH:21].[NH2:18][CH2:17][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[CH2:16][N:8]([CH:7]1[CH2:6][CH2:5][C:4](=[O:20])[NH:3][C:2]1=[O:1])[C:9]2=[O:19]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 219885472-(2,6-Dioxopiperidin-3-yl)-1-oxoisoindoline-4-carbonitrile

Product 1

HCID 219885683-(4-(Aminomethyl)-1-oxoisoindolin-2-yl)piperidine-2,6-dione hydrochlorideYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(2,6-dioxo(3-piperidyl))-1-oxoisoindoline-4-carbonitrile (1.0 g, 3.71 mmol) and 10% Pd/C (0.2 g) in 4N HCl (20 mL) and methanol (600 mL) was hydrogenated at 50 psi for 17 hours. The mixture was filtered through celite and the filtrate was concentrated. The residue was stirred with ether (30 mL) to give 3-[4-(aminomethyl)-1-oxoisoindolin-2-yl]piperidine-2,6-dione hydrochloride (1.1 g, 99%) as a white solid: 1H NMR (DMSO-d6) δ 11.06 (s, 1H), 8.64 (s, 3H), 7.79 (d, J=7.5 Hz, 1H), 7.74 (d, J=7.4 Hz, 1H), 7.59 (t, 7.5 Hz, 1H), 5.21–5.14 (dd, J=5.0 and 13.2 Hz, 1H), 4.69 (d, J=17.4 Hz, 1H), 4.51 (d, J=17.4 Hz, 1H), 4.09 (d, J=4.9 Hz, 2H), 3.00–2.87 (m, 1H), 2.66–2.35 (m, 2H), 2.03–1.98 (m, 1H); 13C NMR (DMSO-d6) δ 172.87, 170.92, 167.77, 141.58, 132.50, 131.88, 129.39, 128.48, 123.25, 51.52, 46.19, 38.39, 31.17, 22.69.

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b6604bbee49d413db01a10987e483767
Source dataset
uspto-grants-2006_08
Patent number
US07091353B2

Linked notes

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