Hydrochloric Acid → N-(4-Amino-butyl)-N'-(3,4-bis-octadec-9-enyloxy-benzyl)-butane-1,4-diamine, tri hydrochloride salt

HRID 604767Notes

Reaction equation

HRID 604767 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:20][CH2:21][CH2:22][CH2:23][NH:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH:41]=[CH:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[C:28]([O:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH:60]=[CH:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH3:69])[CH:27]=1)C(OC(C)(C)C)=O)(C)(C)C.[ClH:71]>C(OCC)(=O)C>[ClH:71].[ClH:71].[ClH:71].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH:41]=[CH:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[C:28]([O:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH:60]=[CH:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH3:69])[CH:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86761294(4-{[4-(3,4-Bis-octadec-9-enyloxy-benzylamino)-butyl]-tert-butoxycarbonyl-amino}-butyl)-carbamic acid tert-butyl ester

Product 1

HCID 131728760N-(4-Amino-butyl)-N'-(3,4-bis-octadec-9-enyloxy-benzyl)-butane-1,4-diamine, tri hydrochloride saltYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

A concentrated solution of the amine 18 (0.17 g, 0.17 mmol) in ethyl acetate was added cooled to 0° C. A total of 4 mL of a freshly prepared saturated solution of HCl in ethyl acetate was added dropwise and the solution stirred for 1 h at room temperature during which time a white precipitate formed. The ethyl acetate was removed in vacuo and the residue co-evaporated with ethyl acetate and chloroform to give the product 25 as a white powder (0.151 g, 98%); 1H NMR (CDCl3/CH3OD 9:1) d 7.13 (s, 1H, aryl), 7.02 (d, 1H, aryl), 6.85 (d, 1H, aryl), 5.33 (m, 4H, olefinic), 4.05 (m, 2H, benzylic), 3.97 (t, 2H, OCH2), 3.04 (m, 6H, 3×CH2) 2.93 (m, 2H, CH2), 2.02 (m, 8H, CH2C═C), 1.90 (m, 8H, 4×CH2), 1.81 (m, 4H, CH2CH2O), 1.47 (m, 4H, 2×CH2), 1.40-1.17 (m, 40H, 20×CH2), 0.89 (t, 6H, CH3); 13C NMR (300 MHz, D2O) δ 148.94, 148.33, 129.26, 129.19, 123.64, 122.52, 113.10, 68.50, 68.39, 49.96, 45.98, 45.43, 39.86, 31.28, 29.18, 29.11, 28.93, 28.86, 28.70, 28.62, 26.64, 26.59, 25.68, 25.62, 24.00, 22.54, 22.46, 22.11, 13.89; HRMS (FAB): theory for C51H96N3O2 (M+1), 782.7497; found (M+1), 782.7495; Anal. (C51H95Cl3N3O2.0.6H2O): C, H, N.

Workup

  1. customformed
  2. customThe ethyl acetate was removed in vacuo

Sources & evidence

ORD record
ord-f63386fa28a64a14a50a5226773c7fde
Source dataset
uspto-grants-2011_03
Patent number
US07910363B1

Reaction notes

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