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

HRID 10064

반응식

HRID 10064 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-b6604bbee49d413db01a10987e483767
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091353B2

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