Hydrochloric Acid → HCID 131737050, compound

HRID 58996Notes

Reaction equation

HRID 58996 reaction equation
[C:1]1([CH2:24][NH:25][CH2:26][CH2:27][CH2:28][NH:29][CH2:30][CH2:31][CH2:32][NH:33][CH2:34][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][CH2:15][NH:16][CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:2]=1.[ClH:41]>>[ClH:41].[C:3]1([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][CH2:15][NH:16][CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:4]=[CH:5][CH:6]=[C:1]([CH2:24][NH:25][CH2:26][CH2:27][CH2:28][NH:29][CH2:30][CH2:31][CH2:32][NH:33][CH2:34][CH:35]2[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]2)[CH:2]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 117718399N1,N1'-(1,3-Phenylenebis(methylene))bis(N3-(3-((cyclohexylmethyl)-amino)propyl)propane-1,3-diamine)

Product 1

HCID 131737050HCID 131737050, compoundYield 67%

Procedure

To the crude N1,N1′-(1,3-phenylenebis-(methylene))bis(N3-(3-((cyclohexylmethyl)amino)propyl)propane-1,3-diamine) from Step 1 was added 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 desire product (1.3 g, 67%) as a white solid. 1H NMR (500 MHz, D2O) δ 7.57 (s, 4H), 4.30 (s, 4H), 3.22 (t, J=7.5 Hz, 4H), 3.18-3.15 (m, 8H), 3.12 (t, J=8.0 Hz, 4H), 2.91 (d, J=7.0 Hz, 4H), 2.18-2.08 (m, 8H), 1.72-1.62 (m, 12H), 1.28-1.11 (m, 6H), 1.03-0.96 (m, 4H). 13C NMR (125 MHz, D2O) δ 131.4, 131.2, 131.0, 130.2, 53.7, 50.8, 48.8, 44.7, 44.6, 44.0, 34.5, 29.7, 25.3, 24.8, 22.6, 22.5. LRMS [M+H]+557.5.

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-87c394ae69544d35ac6dfd1cc6f9b4b0
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

Loading…