1-(2-Methoxyphenyl)piperazine → 1-{3-(p-Fluoroanilino)propyl}-4-(o-methoxyphenyl)piperazine

HRID 328563Notes

Reaction equation

HRID 328563 reaction equation
Cl[CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>O>[F:12][C:9]1[CH:10]=[CH:11][C:6]([NH:5][CH2:4][CH2:3][CH2:2][N:24]2[CH2:23][CH2:22][N:21]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[O:14][CH3:13])[CH2:26][CH2:25]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 12769738(3-Chloropropyl)-(4-fluorophenyl)amine

Product 1

HCID 133142401-{3-(p-Fluoroanilino)propyl}-4-(o-methoxyphenyl)piperazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.9 g of N-(3-chloropropyl)-p-fluoroaniline, 1.9 g of 1-(o-methoxyphenyl)piperazine, 0.5 g of sodium carbonate and 50 ml of dimethylformamide was heated at 80°-90° C for 15 hours. After cooling, the reaction mixture was poured into water and extracted with benzene. The extract was washed with water, dried over sodium sulfate and evaporated under reduced pressure to give 1-{3-(p-fluoroanilino)propyl}-4-(o-methoxyphenyl)piperazine, m.p. 79°-80° C; recrystallized from cyclohexane, m.p. 84°-84.5° C.

Workup

  1. temperaturewas heated at 80°-90° C for 15 hours
  2. temperatureAfter cooling
  3. extractionextracted with benzene
  4. washThe extract was washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3b3007affacf4d99a309c3ff1fc5fb00
Source dataset
uspto-grants-1977_04
Patent number
US04017624

Reaction notes

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