Hydrochloric Acid → N1,N1'-((5-(3-(iso-Butylammonio)propoxy)-1,3-phenylene)bis(methylene))-bis(N3-(3-ammoniopropyl)propane-1,3-diaminium) chloride

HRID 59008Notes

Reaction equation

HRID 59008 reaction equation
[CH2:1]([NH:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH2:26][NH:27][CH2:28][CH2:29][CH2:30][NH:31][CH2:32][CH2:33][CH2:34][NH2:35])[CH:13]=[C:14]([CH2:16][NH:17][CH2:18][CH2:19][CH2:20][NH:21][CH2:22][CH2:23][CH2:24][NH2:25])[CH:15]=1)[CH:2]([CH3:4])[CH3:3].[ClH:36]>>[Cl-:36].[CH2:1]([NH2+:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[C:14]([CH2:16][NH2+:17][CH2:18][CH2:19][CH2:20][NH2+:21][CH2:22][CH2:23][CH2:24][NH3+:25])[CH:13]=[C:12]([CH2:26][NH2+:27][CH2:28][CH2:29][CH2:30][NH2+:31][CH2:32][CH2:33][CH2:34][NH3+:35])[CH:11]=1)[CH:2]([CH3:3])[CH3:4].[Cl-:36].[Cl-:36].[Cl-:36].[Cl-:36].[Cl-:36].[Cl-:36]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 117718429N1,N1'-((5-(3-(iso-Butylamino)propoxy)-1,3-phenylene)bis(methylene))-bis(N3-(3-aminopropyl)propane-1,3-diamine)

Product 1

HCID 131737055N1,N1'-((5-(3-(iso-Butylammonio)propoxy)-1,3-phenylene)bis(methylene))-bis(N3-(3-ammoniopropyl)propane-1,3-diaminium) chlorideYield 43%

Procedure

To N1,N1′-((5-(3-(iso-Butylamino)propoxy)-1,3-phenylene)bis(methylene))bis(N3-(3-aminopropyl)propane-1,3-diamine) from step 6 was added methanolic HCl (50 mL, 1.0M). The reaction mixture was stirred for 1 h, the reaction mixture was concentrated under reduced pressure and the solid collected by vacuum filtration. The solid was washed with Et2O (10 mL) and hot MeOH (10 mL) to afford the desired product (0.14 g, 43%) as a white solid. 1H NMR (500 MHz, D2O) δ ppm 7.21 (s, 1H), 7.19 (s, 2H), 4.30 (s, 4H), 4.23 (t, J=5.5 Hz, 2H), 3.29 (t, J=7 Hz, 2H), 3.25-3.19 (m, 12H), 3.12 (t, J=7.5 Hz, 4H), 2.95 (d, J=7 Hz, 2H), 2.25-2.03 (m, 11H), 1.01 (d, J=7.5 Hz, 6H). 13C NMR (125 MHz, D2O) 158.9, 133.0, 123.7, 117.1, 65.8, 54.8, 50.7, 45.7, 44.7, 44.6, 44.2, 36.7, 25.5, 25.2, 23.7, 22.6, 19.1. LRMS [M+H]+494.4.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. filtrationthe solid collected by vacuum filtration
  3. washThe solid was washed with Et2O (10 mL) and hot MeOH (10 mL)

Sources & evidence

ORD record
ord-12df5d6953f54c70b175c063c14d8425
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

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