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Tetrabutylammonium Fluoride → Tert-butyl 4-[4-(2-hydroxyethyl)benzyl]piperazine-1-carboxylate

HRID 1023327
Notes
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Reaction equation

HRID 1023327 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1[CH:30]=[CH:29][C:14]([CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)=[CH:13][CH:12]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O.O>[OH:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:18][CH2:17]2)=[CH:29][CH:30]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67327082HCID 67327082, compound

Product 1

HCID 67328866Tert-butyl 4-[4-(2-hydroxyethyl)benzyl]piperazine-1-carboxylateYield 77.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
0 °C

Procedure

To a THF (8 mL) solution of tert-butyl 4-[4-(2-{[tert-butyl(dimethyl)silyl]oxy}-ethyl)benzyl]piperazine-1-carboxylate (0.96 g) was added 1.0 M solution of TBAF in THF (2.32 mL) at 0° C. The resultant mixture was stirred at room temperature for 2.5 hours. After cooling to 0° C., the reaction mixture was diluted with AcOEt and water. The organic layer was washed with saturated aqueous NaCl, dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (CH2Cl2/MeOH=40/1) to afford tert-butyl 4-[4-(2-hydroxyethyl)benzyl]piperazine-1-carboxylate (0.55 g) as a colorless oil.

Workup

  1. washThe organic layer was washed with saturated aqueous NaCl
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (CH2Cl2/MeOH=40/1)

Sources & evidence

ORD record
ord-220d01dedcfa460da7db884558a588ec
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08722663B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes