p-Fluorophenethylamine → 2-Chloro-N-[2-(4-fluoro-phenyl)-ethyl]-acetamide

HRID 1796995Notes

Reaction equation

HRID 1796995 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.[Cl:11][CH2:12][C:13](Cl)=[O:14]>C1COCC1>[Cl:11][CH2:12][C:13]([NH:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[O:14]

Participants

4

Reactant 2

HCID 4653p-FluorophenethylamineHCID 6577Chloroacetyl chloride

Product 1

HCID 23845922-Chloro-N-[2-(4-fluoro-phenyl)-ethyl]-acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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

  1. stirringThe reaction mixture was then stirred at room temperature for 1 hour after which time the reaction mixture
  2. customcondensed in vacuo
  3. customquenched with water
  4. extractionextracted with ethyl acetate (3×)
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentration in vacuo, compound 1
  7. customabove was obtained
  8. customfurther without further purification
  9. waitLC/MS=M+H 216.1 at 2.18 minutes

Sources & evidence

ORD record
ord-722cc4d483ea4b8b9bd6def42665c629
Source dataset
uspto-grants-2006_04
Patent number
US07034033B2

Reaction notes

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