Hydrochloric Acid → N1,N1'-([1,1'-biphenyl]-3,5-diylbis(methylene))bis(N3-(3-ammoniopropyl)propane-1,3-diaminium) chloride

HRID 58972Notes

Reaction equation

HRID 58972 reaction equation
[C:1]1([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:6]=[C:5]([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][CH2:15][NH:16]C(=O)OC(C)(C)C)[CH:4]=[C:3]([CH2:24][NH:25][CH2:26][CH2:27][CH2:28][NH:29][CH2:30][CH2:31][CH2:32][NH:33]C(=O)OC(C)(C)C)[CH:2]=1.[ClH:47]>>[Cl-:47].[C:1]1([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:6]=[C:5]([CH2:7][NH2+:8][CH2:9][CH2:10][CH2:11][NH2+:12][CH2:13][CH2:14][CH2:15][NH3+:16])[CH:4]=[C:3]([CH2:24][NH2+:25][CH2:26][CH2:27][CH2:28][NH2+:29][CH2:30][CH2:31][CH2:32][NH3+:33])[CH:2]=1.[Cl-:47].[Cl-:47].[Cl-:47].[Cl-:47].[Cl-:47]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 131737041Di-tert-butyl ((((([1,1'-biphenyl]-3,5-diylbis(methylene))bis(azanediyl))-bis(propane-3,1-diyl))bis(azanediyl))bis(propane-3,1-diyl))dicarbamate

Product 1

HCID 131737042N1,N1'-([1,1'-biphenyl]-3,5-diylbis(methylene))bis(N3-(3-ammoniopropyl)propane-1,3-diaminium) chlorideYield 60%

Procedure

To the crude N1,N1′-([1,1′-biphenyl]-3,5-diylbis(methylene))bis(N3-(3-ammoniopropyl)propane-1,3-diaminium) chloride from Step 2 was added methanolic HCl (150 mL, 1.0 M). The reaction mixture was stirred for 2 h and concentrated under reduced pressure. The solid was collected by vacuum filtration and washed with Et2O (30 mL) and hot MeOH (30 mL) to afford the desired product (6.8 g, 60%) as a white solid. 1H NMR (D2O, 500 MHz) δ ppm 7.85 (s, 2H), 7.74 (d, J=7.5 Hz, 2H), 7.59-7.56 (m, 3H), 7.50-7.49 (m, 1H), 4.38 (s, 4H), 3.29 (t, J=8.0 Hz, 4H), 3.23 (q, J=5.0 Hz, 8H), 3.14 (t, J=8.0 Hz, 4H), 2.25-2.19 (m, 4H), 2.17-2.11 (m, 4H). 13C NMR (125 MHz, D2O) 142.3, 138.8, 132.1, 130.0, 129.5, 129.2, 128.4, 127.0, 50.8, 44.7, 44.6, 44.2, 36.5, 23.7, 22.7. LRMS [M+H]+441.4.

Workup

  1. concentrationconcentrated under reduced pressure
  2. filtrationThe solid was collected by vacuum filtration
  3. washwashed with Et2O (30 mL) and hot MeOH (30 mL)

Sources & evidence

ORD record
ord-9b1dc0ef35b445f0b111be451d5d00a9
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

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