Hydrochloric Acid → HCID 131737056, compound

HRID 59009Notes

Reaction equation

HRID 59009 reaction equation
[CH2:1]([NH:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH2:34][NH:35][CH2:36][CH2:37][CH2:38][NH:39][CH2:40][CH2:41][CH2:42][NH:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH:13]=[C:14]([CH2:16][NH:17][CH2:18][CH2:19][CH2:20][NH:21][CH2:22][CH2:23][CH2:24][NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:15]=1)[CH:2]([CH3:4])[CH3:3].[ClH:52]>>[ClH:52].[CH2:1]([NH:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[C:14]([CH2:16][NH:17][CH2:18][CH2:19][CH2:20][NH:21][CH2:22][CH2:23][CH2:24][NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:13]=[C:12]([CH2:34][NH:35][CH2:36][CH2:37][CH2:38][NH:39][CH2:40][CH2:41][CH2:42][NH:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH:11]=1)[CH:2]([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 117718453N1,N1'-((5-(3-(isobutylamino)propoxy)-1,3-phenylene)bis(methylene))bis(N3-(3-(octylamino)propyl)propane-1,3-diamine)

Product 1

HCID 131737056HCID 131737056, compoundYield 42%

Procedure

To the crude N1,N1′-((5-(3-(isobutylamino)propoxy)-1,3-phenylene)bis(methylene))bis(N3-(3-(octylamino)propyl)propane-1,3-diamine) was added methanolic HCl (100 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 (0.75 g, 42%). 1H NMR (500 MHz, D20) 8 7.21 (s, 1H), 7.20 (s 2H), 4.30 (s, 4H), 4.24 (t, J=5 Hz, 2H), 3.30 (t, J=7 Hz, 2H), 3.26-3.14 (m, 16H), 3.07 (t, J=7 Hz, 4H), 2.96 (d, J=7.5 Hz, 2H), 2.26-2.03 (m, 11H), 1.69 (p, J=6.5 Hz, 4H), 1.38-1.28 (m, 20H), 1.02 (d, J=6.5 Hz, 6H), 0.87 (t, J=5.5 Hz, 6H). 13C NMR (125 MHz, D2O) δ 158.9, 133.0, 123.7, 117.1, 65.8, 54.8, 50.8, 47.9, 45.7, 44.6, 44.6, 44.2, 44.1, 30.9, 28.1, 28.1, 25.6, 25.5, 25.4, 25.2, 22.6, 22.6, 19.1, 13.4.

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-343ded8f96e7400d8ccce2e93e92afcc
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

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