Hydrochloric Acid → N-Anthracen-9-ylmethyl-N'-(3-ethoxy-propyl)-N-ethyl-propane-1,3-diamine, Hydrochloride salt

HRID 12998

Reaction equation

[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15][N:16]([CH2:27][CH3:28])[CH2:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH3:26])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[ClH:29]>C(O)C>[ClH:29].[CH:11]1[C:12]2[C:7](=[CH:6][C:5]3[C:14]([C:13]=2[CH2:15][N:16]([CH2:27][CH3:28])[CH2:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH3:26])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of compound 19 (169 mg, 0.45 mmole) was dissolved in absolute ethanol (13 mL) and stirred at 0° C. for 10 minutes. A 4N HCl solution (22 mL) was added to the reaction mixture dropwise and stirred at 0° C. for 20 minutes and then at room temperature overnight. The solution was concentrated in vacuo to give 21 as a yellow solid in 95% yield. 1H NMR (D2O) δ 8.58 (s, 1H), 8.10 (m, 4H), 7.73 (m, 2H), 7.62 (m, 2H), 5.12 (s, 2H), 3.52 (m, 4H), 3.43 (q, 2H), 3.15 (t, 2H), 2.84 (t, 2H), 2.73 (t, 2H), 1.79 (m, 4H), 1.47 (t, 3H), 1.15 (t, 3H); 13C NMR (D2O): δ 133.9, 133.5, 132.5, 130.9, 128.4, 125.2, 122.1, 69.9, 69.3, 52.7, 52.4, 52.2, 48.1, 47.0, 28.2, 23.5, 17.0, 11.4. HRMS (FAB) calcd for C25H34N2O.2HCl (M+H−2HCl)+ 379.2749, Found 379.2749.

Workup

stirringstirred at 0° C. for 20 minutes
customat room temperature
customovernight
concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record: ord-1f77a0245cd64b56a023f140cd1f7637
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728041B2

Linked notes

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