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

HRID 12997Notes

Reaction equation

HRID 12997 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15][N:16]([CH2:25][CH3:26])[CH2:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][OH:24])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[ClH:27].[CH2:28](O)[CH3:29]>>[ClH:27].[CH:11]1[C:12]2[C:7](=[CH:6][C:5]3[C:14]([C:13]=2[CH2:15][N:16]([CH2:25][CH3:26])[CH2:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][O:24][CH2:28][CH3:29])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 247441943-[3-(Anthracen-9-ylmethyl-ethyl-amino)-propylamino]-propan-1-ol

Product 1

HCID 131728148N-Anthracen-9-ylmethyl-N'-(3-ethoxy-propyl)-N-ethyl-propane-1,3-diamine, Hydrochloride saltYield 95%

Conditions

Temperature
0 °C

Procedure

A solution of compound 18 (200 mg, 0.57 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 20 as a yellow solid in 95% yield. 1H NMR (D2O) δ 8.50 (s, 1H), 8.06 (m, 4H), 7.73 (m, 2H), 7.62 (m, 2H), 4.98 (s, 2H), 3.64 (t, 2H), 3.39 (q, 2H), 3.13 (t, 2H), 2.90 (t, 2H), 2.76 (t, 2H), 1.79 (q, 2H), 1.44 (m, 5H); 13C NMR (D2O): δ 133.8, 133.4, 132.4, 130.8, 128.3, 125.1, 121.8, 61.4, 52.4, 52.1, 52.0, 48.0, 47.0, 30.5, 23.4, 11.3. HRMS (FAB) calcd for C23H3ON2O.2HCl (M+H−2HCl)+ 351.2431, Found 351.2428.

Workup

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

Sources & evidence

ORD record
ord-50a85d6b589448ee8061f291906fe7d7
Source dataset
uspto-grants-2010_06
Patent number
US07728041B2

Reaction notes

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