Pyridine → 1-(2-Chloroethyl)-4-(2-fluorophenyl)piperazine

HRID 49032Notes

Reaction equation

HRID 49032 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[CH2:10][CH2:9]1.N1C=CC=CC=1>C1C=CC=CC=1>[Cl:3][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 206351751-(2-Hydroxyethyl)-4-(2-fluorophenyl)piperazine

Product 1

HCID 220749171-(2-Chloroethyl)-4-(2-fluorophenyl)piperazineYield 18%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Thionyl chloride (1 mL) was added dropwise to an ice-cooled solution of 1-(2-hydroxyethyl)-4-(2-fluorophenyl)piperazine (300 mg) and pyridine (1 mL) in benzene (20 mL). After 30 minutes the solution was brought to room temperature and then the flask was immersed in a 60° C. oil bath for 1 hour. The layers were separated and the aqueous fraction was extracted with ethyl acetate (2×20 mL). The combined organic fractions were dried over sodium sulfate and the solvent was removed in vacuo, giving the desired product as a yellow solid (58.6 mg, 18%). ESI-MS m/z 243 (MH+).

Workup

  1. customwas immersed in a 60° C.
  2. customfor 1 hour
  3. customThe layers were separated
  4. extractionthe aqueous fraction was extracted with ethyl acetate (2×20 mL)
  5. dry with materialThe combined organic fractions were dried over sodium sulfate
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-532bea074d9349e1aa5ec78b82267267
Source dataset
uspto-grants-2004_03
Patent number
US06706716B2

Reaction notes

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