Hydrochloric Acid → N1-(3,4-Bis-octadec-9-enyloxy-benzyl)-octane-1,8-diamine, dihydrochloride salt

HRID 604765Notes

Reaction equation

HRID 604765 reaction equation
[CH2:1]([O:19][C:20]1[CH:21]=[C:22]([CH:34]=[CH:35][C:36]=1[O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH:46]=[CH:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH2:23][NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][NH2:33])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[ClH:56]>C(OCC)(=O)C>[ClH:56].[ClH:56].[CH2:1]([O:19][C:20]1[CH:21]=[C:22]([CH:34]=[CH:35][C:36]=1[O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH:46]=[CH:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH2:23][NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][NH2:33])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 123142334N1-(3,4-bis-octadec-9-enyloxy-benzyl)-octane-1,8-diamine

Product 1

HCID 131728758N1-(3,4-Bis-octadec-9-enyloxy-benzyl)-octane-1,8-diamine, dihydrochloride salt

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

A concentrated solution of the amine 16 (0.097 g, 0.13 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 23 as an off white powder (0.104 g, 98%); 1H NMR (CDCl3) d 7.24 (s, 1H, aryl), 7.05 (d, 1H, aryl), 6.85 (d, 1H, aryl), 5.35 (m, 4H, olefinic), 4.07 (q, 4H, OCH2), 3.95 (t, 2H, benzylic), 3.07 (m, 2H, CH2) 2.79 (m, 2H, CH2), 2.05 (m, 8H, CH2C═C), 1.82 (m, 8H, CH2CH2O, 2×CH2), 1.58-1.21 (m, 52H, 26×CH2), 0.89 (t, 6H, CH3); 13C NMR (300 MHz, CDCl3) d 149.36, 148.78, 130.85, 130.33, 129.74, 122.23, 115.56, 113.45, 69.56, 69.32, 51.56, 51.15, 45.96, 39.86, 32.53, 30.44, 30.44, 30.23, 30.12, 30.00, 29.71, 27.61, 27.51, 27.10, 26.83, 26.69, 24.82, 23.77, 23.08, 14.54; HRMS (FAB): theory for C51H95N2O2 (M+1), 767.7394; found (M+1), 767.7419; Anal. (C51H96Cl2N2O2.0.3H2O): C, H, N.

Workup

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

Sources & evidence

ORD record
ord-bf36a61918c04cc3a251bf5b683b1e3a
Source dataset
uspto-grants-2011_03
Patent number
US07910363B1

Reaction notes

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