Ammonium Chloride → 16-(2,5-Dimethoxyphenylamino)hexadecan-1-ol

HRID 1367772Notes

Reaction equation

HRID 1367772 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:27]=1[O:34][CH3:35])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>O1CCCC1>[CH3:35][O:34][C:27]1[CH:28]=[CH:29][C:30]([O:32][CH3:33])=[CH:31][C:26]=1[NH:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:8]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 66731777HCID 66731777, compound

Product 1

HCID 4441400016-(2,5-Dimethoxyphenylamino)hexadecan-1-olYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[16-(t-Butyldimethylsilanyloxy)hexadecyl]-(2,5-dimethoxyphenyl)amine (144.2 mg) was dissolved in tetrahydrofuran, and then tetrabutylammonium fluoride (1 M solution in THF) (3.4 ml) was added to this solution. The reaction mixture was stirred for one day at room temperature. Saturated ammonium chloride solution was added to the reaction mixture, which was then extracted three times with diethyl ether. The organic layer was washed with saline solution and dried over magnesium sulfate, and the solvent was distilled off at reduced pressure. Purification of the residue by silica gel flash chromatography (heptane:ethyl acetate=6:4) gave 16-(2,5-dimethoxyphenylamino)hexadecan-1-ol as white crystals at an 81% yield.

Workup

  1. extractionwas then extracted three times with diethyl ether
  2. washThe organic layer was washed with saline solution
  3. dry with materialdried over magnesium sulfate
  4. distillationthe solvent was distilled off at reduced pressure
  5. customPurification of the residue by silica gel flash chromatography (heptane:ethyl acetate=6:4)

Sources & evidence

ORD record
ord-e0e0e45ab01e411da09468906643d130
Source dataset
uspto-grants-2011_02
Patent number
US07893304B2

Reaction notes

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