Toluene → 4-Fluoro-N-[3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl]benzamide

HRID 638161Notes

Reaction equation

HRID 638161 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.Cl[CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:28])[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1.C1(C)C=CC=CC=1>C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:28])[C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 13461-(2-Methoxyphenyl)piperazineHCID 3755026HCID 3755026, compound

Product 1

HCID 133185024-Fluoro-N-[3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl]benzamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 1.92 g (0.01 mol) of 1-(2-methoxyphenyl)-piperazine and 2.15 g (0.01 mol) of N-(3-chloropropyl)-4-fluorobenzamide was added to a mixture of toluene (20 ml) and triethylamine (2 ml) under agitation. The resulting mixture was gradually heated to the refluxing temperature at which the mixture was held for 5 hours. After completion of the reaction, the mixture was cooled and the precipitating salt was filtered off. The filtrate was extracted with 20 ml of benzene, and the extract was washed first with saturated aqueous sodium bicarbonate, then washed with water twice. By drying with anhydrous magnesium sulfate and subsequent concentration, 1-(2-methoxyphenyl)-4-[3-(4-fluorobenzoyl)aminopropyl]piperazine was produced as an oily substance. The oil was dissolved in methanol (30 ml) and the solution was saturated with hydrogen chloride gas. Upon concentration of the saturated solution, a crystal of the piperazine in hydrochloride form was obtained (2.9 g). m.p. 231.7° C. (recrystallized from ethanol).

Workup

  1. temperatureThe resulting mixture was gradually heated to the refluxing temperature at which the mixture
  2. customAfter completion of the reaction
  3. temperaturethe mixture was cooled
  4. filtrationthe precipitating salt was filtered off
  5. extractionThe filtrate was extracted with 20 ml of benzene
  6. washthe extract was washed first with saturated aqueous sodium bicarbonate
  7. washwashed with water twice
  8. dry with materialBy drying with anhydrous magnesium sulfate and subsequent concentration

Sources & evidence

ORD record
ord-9166e23d648444639366e63c8e33f6fe
Source dataset
uspto-grants-1985_12
Patent number
US04560686

Reaction notes

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