Hydrochloric Acid → HCID 131737049, compound

HRID 58995Notes

Reaction equation

HRID 58995 reaction equation
[CH2:1]([CH:3]([CH2:40][CH3:41])[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:26][NH:27][CH2:28][CH2:29][CH2:30][NH:31][CH2:32][CH2:33][CH2:34][NH:35][CH2:36][CH:37]([CH3:39])[CH3:38])[CH:9]=[C:10]([CH2:12][NH:13][CH2:14][CH2:15][CH2:16][NH:17][CH2:18][CH2:19][CH2:20][NH:21][CH2:22][CH:23]([CH3:25])[CH3:24])[CH:11]=1)[CH3:2].[ClH:42]>>[Cl-:42].[CH2:40]([CH:3]([CH2:1][CH3:2])[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:26][NH2+:27][CH2:28][CH2:29][CH2:30][NH2+:31][CH2:32][CH2:33][CH2:34][NH2+:35][CH2:36][CH:37]([CH3:39])[CH3:38])[CH:9]=[C:10]([CH2:12][NH2+:13][CH2:14][CH2:15][CH2:16][NH2+:17][CH2:18][CH2:19][CH2:20][NH2+:21][CH2:22][CH:23]([CH3:24])[CH3:25])[CH:11]=1)[CH3:41].[Cl-:42].[Cl-:42].[Cl-:42].[Cl-:42].[Cl-:42]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 117718459HCID 117718459, compound

Product 1

HCID 131737049HCID 131737049, compoundYield 59%

Procedure

To N1,N1′-((5-(2-ethylbutoxy)-1,3-phenylene)bis(methylene))bis(N3-(3-(isobutylamino)propyl) propane-1,3-diamine) from step 4 was which 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 (0.42 g, 59%) as a white solid. 1H NMR (500 MHz, D2O) δ 7.20 (s, 2H), 7.18 (s, 1H), 4.29 (s, 4H), 4.05 (d, J=6.0 Hz, 2H), 3.25-3.15 (m, 16H), 2.94 (d, J=7.0 Hz, 2H), 2.21-2.12 (m, 8H), 2.07-1.99 (m, 2H), 1.72 (p, J=6.5 Hz, 1H), 1.50-1.43 (m, 4H), 1.00 (d, J=7.0 Hz, 12H), 0.92 (t, J=6.0 Hz, 6H). 13C NMR (125 MHz, D2O) δ 159.6, 132.9, 123.4, 117.4, 71.4, 54.8, 50.8, 44.7, 44.6, 44.6, 44.1, 40.1, 25.5, 22.6, 22.5, 19.0, 10.2. LRMS [M+H]+577.6.

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-5cae79eff55b4b39bc8fb3f53efa4cd0
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

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