p-Fluorophenethylamine → 2-Chloro-N-[2-(4-fluoro-phenyl)-ethyl]-acetamide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Cl:20][CH2:21][C:22](Cl)=[O:23]>C1COCC1>[Cl:20][CH2:21][C:22]([NH:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[O:23]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 4-fluorophenylethylamine (1.0 equivalent) in dried THF was added Hunig's base (DIEA) (1 equivalent). The mixture was then stirred for 3 minutes at 0° C. Thereafter, a solution of chloroacetylchloride (1.0 equivalent) in THF was added via a syringe over a period of 7 minutes. The reaction mixture was then stirred at room temperature for 1 hour after which time the reaction mixture was condensed in vacuo, quenched with water, extracted with ethyl acetate (3×) and dried over Na2SO4. After concentration in vacuo, compound 1 shown above was obtained, which was carried on further without further purification. LC/MS=M+H 216.1 at 2.18 minutes.
Workup
- stirringThe reaction mixture was then stirred at room temperature for 1 hour after which time the reaction mixture
- customcondensed in vacuo
- customquenched with water
- extractionextracted with ethyl acetate (3×)
- dry with materialdried over Na2SO4
- concentrationAfter concentration in vacuo, compound 1
- customabove was obtained
- customfurther without further purification
- waitLC/MS=M+H 216.1 at 2.18 minutes
Sources & evidence
- ORD record
- ord-9a339c9a09714690a742bf95be7468a5
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07625909B2
Reaction notes
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