Toluene → 1-(9-Oxo-2-fluorenylcarbonyl)-4-(3,4,5-trimethoxybenzyl)piperazine

HRID 1638795Notes

Reaction equation

HRID 1638795 reaction equation
[O:1]=[C:2]1[C:14]2[CH:13]=[C:12]([C:15](O)=[O:16])[CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.C1(C)C=CC=CC=1.S(Cl)(Cl)=O.Cl.Cl.[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:43]=[C:44]([O:48][CH3:49])[C:45]=1[O:46][CH3:47])[CH2:36][N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1>O.CN(C)C=O.C(N(CC)CC)C>[O:1]=[C:2]1[C:14]2[CH:13]=[C:12]([C:15]([N:40]3[CH2:41][CH2:42][N:37]([CH2:36][C:35]4[CH:34]=[C:33]([O:32][CH3:31])[C:45]([O:46][CH3:47])=[C:44]([O:48][CH3:49])[CH:43]=4)[CH2:38][CH2:39]3)=[O:16])[CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

8

Reactant 4

HCID 1140Toluene2×HCID 24386Thionyl ChlorideHCID 69913Fluorenone-2-carboxylic acidHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochloride

Product 1

HCID 146761681-(9-Oxo-2-fluorenylcarbonyl)-4-(3,4,5-trimethoxybenzyl)piperazineYield 52.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 9-oxo-2-fluorene carboxylic acid (1 g), toluene (10 ml), and thionyl chloride (3 ml) is heated for one hour under reflux. The mixture is evaporated to dryness. To the residue is added toluene (10 ml), and the mixture is again evaporated to dryness. Thus-obtained yellow powder is mixed with toluene (50 ml), and the mixture is added to a mixture of 1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (1.8 g), triethylamine (4.3 g) and N,N-dimethylformamide (20 ml). The resulting mixture is left standing at room temperature for 30 minutes and treated with water (300 ml). The whole mixture is extracted with ethyl acetate (500 ml). The organic layer is washed with water, dried and concentrated to afford 1-(9-oxo-2-fluorenylcarbonyl)-4-(3,4,5-trimethoxybenzyl)piperazine (1.1 g) as pale yellow crystals, m.p. 166°-168° C.

Workup

  1. temperatureis heated for one hour
  2. temperatureunder reflux
  3. customThe mixture is evaporated to dryness
  4. additionTo the residue is added toluene (10 ml)
  5. customthe mixture is again evaporated to dryness
  6. customThus-obtained yellow powder
  7. waitThe resulting mixture is left
  8. extractionThe whole mixture is extracted with ethyl acetate (500 ml)
  9. washThe organic layer is washed with water
  10. customdried
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-982faac678124b75aa9149b78318a17c
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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