Ammonium Chloride → 5-{4-Hydroxy-2-[4-(2-piperidin-1-ylethoxy)phenylamino]phenyl}indan-1-ol

HRID 1434093Notes

Reaction equation

HRID 1434093 reaction equation
[Si]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:31]2[CH:32]=[C:33]3[C:37](=[CH:38][CH:39]=2)[CH:36]([O:40][Si](C(C)(C)C)(C)C)[CH2:35][CH2:34]3)=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:18][CH:17]=2)[CH:14]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>O1CCCC1>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:31]2[CH:32]=[C:33]3[C:37](=[CH:38][CH:39]=2)[CH:36]([OH:40])[CH2:35][CH2:34]3)=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:18][CH:17]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 57933787{5-(tert-Butyldimethylsilyloxy)-2-[1-(tert-butyldimethylsilyloxy)indan-5-yl]phenyl}[4-(2-piperidin-1-ylethoxy)phenyl]amine

Product 1

HCID 579345935-{4-Hydroxy-2-[4-(2-piperidin-1-ylethoxy)phenylamino]phenyl}indan-1-olYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {5-(tert-butyldimethylsilyloxy)-2-[1-(tert-butyldimethylsilyloxy)indan-5-yl]phenyl}[4-(2-piperidin-1-ylethoxy)phenyl]amine (590 mg) in tetrahydrofuran (8 ml) was added tetrabutylammonium fluoride (1.0 M solution in tetrahydrofuran) (3 ml), and the solution was stirred for 3 hours at room temperature. A saturated aqueous solution of ammonium chloride was added thereto followed by stirring, the solution was extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (ethyl acetate-methanol system) to provide the title compound (308 mg).

Workup

  1. stirringby stirring
  2. extractionthe solution was extracted with ethyl acetate
  3. washsequentially washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by NH silica gel column chromatography (ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-3b514bae67d34008829c18cb4ae09810
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

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