Diethyl Ether → 2-[4-(5-Bromothiazole-2-yl)-2,6-dimethyl piperazine-1-yl]ethanol
Reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]1[CH:10]([CH3:11])[CH2:9][N:8]([C:12]2[S:13][C:14]([Br:17])=[CH:15][N:16]=2)[CH2:7][CH:6]1[CH3:18].[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].C(OCC)C>O1CCCC1>[Br:17][C:14]1[S:13][C:12]([N:8]2[CH2:7][CH:6]([CH3:18])[N:5]([CH2:4][CH2:3][OH:2])[CH:10]([CH3:11])[CH2:9]2)=[N:16][CH:15]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of [4-(5-bromothiazole-2-yl)-2,6-dimethyl piperazine-1-yl]acetic acid methyl ester (20.1 g) in tetrahydrofuran (300 mL) was added dropwise diisobutyl aluminium hydride (1M toluene solution, 200 mL) at −78° C. The mixture was stirred at −78° C. for 3.5 hours. To the reaction solution were added aqueous ammonium chloride solution (150 mL) and diethyl ether (45 mL). The insoluble material was filtrated. The filtrate was extracted diethyl ether. The organic layer was washed with water and brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatograph on silica gel to give the title compound (13.2 g). Yield: 71%.
Workup
- filtrationThe insoluble material was filtrated
- extractionThe filtrate was extracted diethyl ether
- washThe organic layer was washed with water and brine
- dry with materialdried over magnesium sulphate
- customThe solvent was evaporated under reduced pressure
- customThe residue was purified by column chromatograph on silica gel
Sources & evidence
- ORD record
- ord-c6b3a8193c2a4cd99cdb65a047a1fc37
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08097610B2
Reaction notes
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