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

HRID 58987Notes

Reaction equation

HRID 58987 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][CH:18]([CH3:20])[CH3:19])[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][CH:32]([CH3:34])[CH3:33])[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][CH:32]([CH3:33])[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][CH:18]([CH3:19])[CH3:20])[CH:6]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 117718407N1,N1'-([1,1'-Biphenyl]-3,5-diylbis(methylene))bis(N3-(3-(isobutylamino)propyl)propane-1,3-diamine)

Product 1

HCID 131737048N1,N1'-([1,1'-Biphenyl]-3,5-diylbis(methylene))bis(N3-(3-(isobutylamino)propyl)propane-1,3-diamine) hydrochloride saltYield 50%

Procedure

To the crude N1,N1′-([1,1′-biphenyl]-3,5-diylbis(methylene))bis(N3-(3-(isobutylamino)propyl)propane-1,3-diamine) was added methanolic HCl (200 mL, 1.0M). The reaction mixture was stirred at rt for 1 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 as a white solid (3.07 g, 50%). 1H NMR (500 MHz, D2O) δ 7.87 (s, 2H), 7.75 (d, J=7.5, 2H), 7.59-7.48 (m, 4H), 4.39 (s, 4H), 3.26 (t, J=8.0 Hz, 4H), 3.21-3.12 (m, 12H), 2.92 (d, J=7.0 Hz, 4H), 2.21-2.10 (in, 8H), 2.01 (sept, J=7.0 Hz, 2H), 0.99 (d, J=7.0 Hz, 12H). 13C NMR (125 MHz, D2O) δ 142.8, 139.1, 132.4, 130.1, 129.8, 129.5, 128.7, 127.3, 55.1, 51.1, 44.9, 44.8, 44.4, 25.8, 22.8, 22.7, 19.2. 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-e26534b36f4a470b95f5bd311f148fcb
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

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