4-Aminobenzyl alcohol → N-(4-hydroxymethylphenyl) 3,4,5-tris(octadecyloxy)cyclohexylcarboxamide

HRID 1502552Notes

Reaction equation

HRID 1502552 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.[CH2:20]([O:38][CH:39]1[CH:44]([O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])[CH:43]([O:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH3:82])[CH2:42][CH:41]([C:83](O)=[O:84])[CH2:40]1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].CCN=C=NCCCN(C)C.Cl>C(Cl)(Cl)Cl.O>[OH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([NH:1][C:83]([CH:41]2[CH2:42][CH:43]([O:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH3:82])[CH:44]([O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])[CH:39]([O:38][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:40]2)=[O:84])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 693314-Aminobenzyl alcoholHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 873243853,4,5-Tris(octadecyloxy)cyclohexylcarboxylic acid

Product 1

HCID 53257322N-(4-hydroxymethylphenyl) 3,4,5-tris(octadecyloxy)cyclohexylcarboxamideYield 45.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

4-Aminobenzyl alcohol (282 mg, 2.29 mmol) was dissolved in chloroform (40 ml), and HOBt (32 mg, 0.23 mmol) and 3,4,5-tris(octadecyloxy)cyclohexylcarboxylic acid (1.11 g, 1.19 mmol) were added. EDC.HCl (356 mg, 1.86 mmol) and pure water (120 μl) were added under ice-cooling, and the mixture was stirred at room temperature overnight. After completion of the reaction, the solvent was evaporated, and the residue was precipitated with acetonitrile (10 ml), and isolated by silica gel column chromatography (chloroform/ethyl acetate=10:1) to give N-(4-hydroxymethylphenyl) 3,4,5-tris(octadecyloxy)cyclohexylcarboxamide (556 mg, 0.54 mmol, yield 45%).

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated
  4. customthe residue was precipitated with acetonitrile (10 ml)
  5. customisolated by silica gel column chromatography (chloroform/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-cb0d7789546a4e4ebe8460dcb6b0c4f9
Source dataset
uspto-grants-2015_12
Patent number
US09206230B2

Reaction notes

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