Hydrochloric Acid → N1,N1'-([1,1'-biphenyl]-3,5-diylbis(methylene))bis(N3-(3-(butylamino)propyl)propane-1,3-diamine) hydrochloride salt

HRID 58982Notes

Reaction equation

HRID 58982 reaction equation
[C:1]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=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][CH2:17][CH2:18][CH2:19][CH3:20])[CH:4]=[C:3]([CH2:21][NH:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:27][CH2:28][CH2:29][NH:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:2]=1.[ClH:41]>>[ClH:41].[C:1]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:2]=[C:3]([CH2:21][NH:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:27][CH2:28][CH2:29][NH:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:4]=[C:5]([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][CH2:15][NH:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:6]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 117718406N1,N1'-([1,1'-biphenyl]-3,5-diylbis(methylene))bis(N3-(3-(butylamino)propyl)propane-1,3-diamine)

Product 1

HCID 122685125N1,N1'-([1,1'-biphenyl]-3,5-diylbis(methylene))bis(N3-(3-(butylamino)propyl)propane-1,3-diamine) hydrochloride saltYield 51%

Procedure

To the crude N1,N1′-([1,1′-biphenyl]-3,5-diylbis(methylene))bis(N3-(3-(butylamino)propyl)propane-1,3-diamine) from step 2 was subjected to acidification with methanolic HCl (100 mL, 1.0M). The reaction mixture stirred at rt for 2 h. The reaction mixture was concentrated under reduced pressure and the solid was collected by vacuum filtration and washed with Et2O (50 mL) and hot MeOH (50 mL) to afford the desired product (1.24 g, 51%) as a white solid. 1H NMR (500 MHz, D2O) δ 7.83 (s, 2H), 7.71 (d, J=7.5 Hz, 2H), 7.55-7.52 (m, 3H), 7.49-7.45 (m, 1H), 4.35 (s, 4H), 3.26 (t, J=7.5 Hz, 4H), 3.21-3.16 (m, 8H), 3.14 (t, J=8.0 Hz, 4H), 3.05 (t, J=8.0 Hz, 4H), 2.21-2.10 (m, 8H), 1.65 (quint, J=7.0 Hz, 4H), 1.37 (sext, J=8.0 Hz, 4H), 0.91 (t, J=7.0 Hz, 6H). 13C NMR (125 MHz, D2O) δ 142.5, 138.9, 132.3, 130.3, 129.8, 129.5, 128.7, 127.3, 51.0, 47.8, 44.9, 44.5, 44.4, 27.7, 22.9, 22.9, 19.3, 13.0. LRMS [M+H]+553.5.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. filtrationthe solid was collected by vacuum filtration
  3. washwashed with Et2O (50 mL) and hot MeOH (50 mL)

Sources & evidence

ORD record
ord-c735b14bc38b457d8308925908dd771d
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

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