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

HRID 10064

反応式

HRID 10064 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-b6604bbee49d413db01a10987e483767
出典データセット
uspto-grants-2006_08
特許番号
US07091353B2

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