Hydrochloric Acid → N1-(3,4-Bis-octadec-9-enyloxy-benzyl)-butane-1,4-diamine, dihydrochloride salt

HRID 604764Notes

Reaction equation

HRID 604764 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=[CH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[C:16]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH:48]=[CH:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH:15]=1)(C)(C)C.[ClH:59]>C(OCC)(=O)C>[ClH:59].[ClH:59].[CH2:40]([O:39][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=1[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=[CH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:13][NH:12][CH2:11][CH2:10][CH2:9][CH2:8][NH2:7])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH:48]=[CH:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86761293[4-(3,4-Bis-octadec-9-enyloxy-benzylamino)-butyl]-carbamic acid tert-butyl ester

Product 1

HCID 131728757N1-(3,4-Bis-octadec-9-enyloxy-benzyl)-butane-1,4-diamine, dihydrochloride salt

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

A concentrated solution of the amine 15 (0.158 g, 0.19 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 22 as an off white powder (0.15 g, 98%); 1H NMR (500 MHz, CDCl3) d 9.50 (br s, 2H, R2N+H2), 8.22 (br s, 3H, RN+H3), 7.24 (s, 1H, aryl), 7.05 (d, 1H, aryl), 6.82 (d, 1H, aryl), 5.34 (m, 4H, olefinic), 4.02 (q, 4H, OCH2), 3.93 (t, 2H, benzylic), 3.07 (m, 2H, CH2) 2.81 (m, 2H, CH2), 2.01 (m, 8H, CH2C═C), 1.95 (m, 2H, CH2), 1.85 (m, 2H, CH2), 1.78 (m, 4H, CH2CH2O), 1.45 (m, 4H, 2×CH2), 1.38-1.20 (m, 40H, 20×CH2), 0.89 (t, 6H, CH3); 13C NMR (300 MHz, CDCl3) d 150.00, 149.37, 130.12, 130.09, 129.95, 122.58, 115.81, 113.49, 69.63, 69.38, 51.44, 51.06, 45.80, 39.63, 32.29, 30.24, 30.21, 30.16, 30.00, 29.93, 29.71, 27.61, 26.63, 26.49, 24.83, 23.75, 23.08, 14.54; HRMS (FAB): theory for C47H87N2O2 (M+1), 711.6768; found (M+1), 711.6827; Anal. (C47H88Cl2N2O4.1.2H2O): C, H, N.

Workup

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

Sources & evidence

ORD record
ord-1af7ae20d8f141329ae7b6694b89a14d
Source dataset
uspto-grants-2011_03
Patent number
US07910363B1

Reaction notes

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