Reaction equation
[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([CH:12]([NH:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:13][OH:14])=[CH:4][C:3]=1[Cl:20]>C(OCC)C.C(O)C>[ClH:20].[NH2:1][C:2]1[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][C:5]([CH:12]([NH:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH2:13][OH:14])=[CH:4][C:3]=1[Cl:20]Participants
Procedure
1.0 g of 2-(4-amino-3-chloro-5-trifluoromethylphenyl)-2-tert-butylaminoethanol was dissolved in 20 ml of diethyl ether and filtered. Saturated solution of hydrogen chloride in isopropanol was added dropwise and acidified to pH=2. The precipitate was collected by filtration, washed with anhydrous ether, and dried to give crude 2-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-tert-butylaminoethanol hydrochloride. The crude product was dissolved in absolute ethanol at a ratio of 1:5 w/v. Filtered, anhydrous ether was added dropwise until small amount of crystals was precipitated. Lyophilized and filtered to give 2-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-tert-butylaminoethanol hydrochloride. Yield 80–90%; melting point 205–206° C. (dec). 1H-NMR (DMSO-d6) δ:1.24 (9H, s), 3.77(2H, d), 4.42–4.44(1H, m), 7.72(1H, s), 7.87(1H, s).
Workup
- filtrationfiltered
- additionSaturated solution of hydrogen chloride in isopropanol was added dropwise
- filtrationThe precipitate was collected by filtration
- washwashed with anhydrous ether
- customdried
- customto give crude 2-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-tert-butylaminoethanol hydrochloride
- filtrationFiltered
- additionanhydrous ether was added dropwise until small amount of crystals
- customwas precipitated
- filtrationLyophilized and filtered
Sources & evidence
- ORD record
- ord-b0b6eaf0998a4f67af847dbabab1ce48
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07098364B2
Linked notes
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