Hydrochloric Acid → N1,N1'-((5-Butoxy-1,3-phenylene)bis(methylene))bis(N3-(3-aminopropyl)propane-1,3-diamine), hydrochloride salt

HRID 58979Notes

Reaction equation

HRID 58979 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH2:29][NH:30][CH2:31][CH2:32][CH2:33][NH:34][CH2:35][CH2:36][CH2:37][NH:38]C(=O)OC(C)(C)C)[CH:9]=[C:10]([CH2:12][NH:13][CH2:14][CH2:15][CH2:16][NH:17][CH2:18][CH2:19][CH2:20][NH:21]C(=O)OC(C)(C)C)[CH:11]=1)[CH2:2][CH2:3][CH3:4].[ClH:46]>>[ClH:46].[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH2:29][NH:30][CH2:31][CH2:32][CH2:33][NH:34][CH2:35][CH2:36][CH2:37][NH2:38])[CH:9]=[C:10]([CH2:12][NH:13][CH2:14][CH2:15][CH2:16][NH:17][CH2:18][CH2:19][CH2:20][NH2:21])[CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 131737045Di-tert-butyl ((((((5-butoxy-1,3-phenylene)bis(methylene))bis(azanediyl))-bis(propane-3,1-diyl))bis(azanediyl))bis(propane-3,1-diyl))dicarbamate

Product 1

HCID 131737046N1,N1'-((5-Butoxy-1,3-phenylene)bis(methylene))bis(N3-(3-aminopropyl)propane-1,3-diamine), hydrochloride saltYield 48%

Procedure

To the crude di-tert-butyl ((((((5-butoxy-1,3-phenylene)bis(methylene))bis(azanediyl))bis(propane-3,1-diyl))bis(azanediyl))-bis(propane-3,1-diyl))dicarbamate from Step 4 was added methanolic HCl (50 mL, 1.0 M). The reaction mixture was stirred for 2 h and concentrated under reduced pressure. The solid was collected by vacuum filtration and washed with Et2O (10 mL) and hot MeOH (10 mL) to afford the desired product (0.27 g, 48%) as a white solid. 1H NMR (500 MHz, D2O) δ ppm 7.20 (s, 3H), 4.30 (s, 4H), 4.15 (t, J=6.5 Hz, 2H), 3.26-3.20 (m, 12H), 3.14 (t, J=7.5 Hz, 4H), 2.22-2.10 (m, 8H), 1.79 (quint, J=6.5 Hz, 2H), 1.48 (sext, J=7.5 Hz, 2H), 0.96 (t, J=7 Hz, 3H). 13C NMR (125 MHz, D2O) 159.2, 132.9, 123.5, 117.3, 68.8, 50.8, 44.7, 44.6, 44.1, 36.5, 30.3, 23.7, 22.6, 18.5, 13.0. LRMS [M+H]+437.4.

Workup

  1. concentrationconcentrated under reduced pressure
  2. filtrationThe solid was collected by vacuum filtration
  3. washwashed with Et2O (10 mL) and hot MeOH (10 mL)

Sources & evidence

ORD record
ord-0a54d26a509e4a16a5e1059590b2975c
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

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