Hydrochloric Acid → 2-Methoxy-4-[2',2',2'-tris(octadecyloxymethyl)ethoxy]benzylamine

HRID 537610Notes

Reaction equation

HRID 537610 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH2:13][C:14]([CH2:55][O:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH3:74])([CH2:35][O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:15][O:16][CH2:17][CH2:18][CH2:19][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][CH3:34])[CH:9]=[CH:8][C:4]=1[CH:5]=[N:6]O.Cl>C1COCC1>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH2:13][C:14]([CH2:55][O:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH3:74])([CH2:35][O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:15][O:16][CH2:17][CH2:18][CH2:19][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][CH3:34])[CH:9]=[CH:8][C:4]=1[CH2:5][NH2:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866548912-Methoxy-4-[2,2,2-tris(octadecyloxymethyl)ethoxy]benzaldoxime

Product 1

HCID 532588112-Methoxy-4-[2',2',2'-tris(octadecyloxymethyl)ethoxy]benzylamineYield 107.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Methoxy-4-[2′,2′,2′-tris(octadecyloxymethyl)ethoxy]benzaldoxime (40 mg, 0.038 mmol) was dissolved in THF (1 ml), diisobutylaluminum hydride (DIBAL)-toluene solution (127 μl, 0.13 mmol) was added dropwise, and the mixture was stirred for 2.5 hr. 1N Hydrochloric acid (2 ml) was added dropwise to the reaction mixture to quench the reaction, and the mixture was extracted with chloroform (2 ml) and washed with 10% aqueous sodium carbonate solution (1 ml). The solvent was evaporated, and acetonitrile (1 ml) was added to the residue. The precipitate was collected by filtration, and purified by silica gel chromatography to give 2-methoxy-4-[2′,2′,2′-tris(octadecyloxymethyl)ethoxy]benzylamine (43 mg, 0.041 mmol, 85%).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with chloroform (2 ml)
  4. washwashed with 10% aqueous sodium carbonate solution (1 ml)
  5. customThe solvent was evaporated
  6. additionacetonitrile (1 ml) was added to the residue
  7. filtrationThe precipitate was collected by filtration
  8. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-06c250af5bea4b8ab744a940c4494aff
Source dataset
uspto-grants-2014_10
Patent number
US08859732B2

Reaction notes

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