1-(4-Fluorobenzyl)piperazine → N-Benzyloxycarbonyl-3-[{4-(4-fluorobenzyl)-piperazin-1-yl}-beta-hydroxypropyloxy]-4-methoxybenzylamine

HRID 583106Notes

Reaction equation

HRID 583106 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH2:22][CH:23]2[O:25][CH2:24]2)[CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:26][C:27]1[CH:39]=[CH:38][C:30]([CH2:31][N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[CH:29][CH:28]=1>C(O)C>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH2:22][CH:23]([OH:25])[CH2:24][N:35]2[CH2:34][CH2:33][N:32]([CH2:31][C:30]3[CH:38]=[CH:39][C:27]([F:26])=[CH:28][CH:29]=3)[CH2:37][CH2:36]2)[CH:14]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7965631-(4-Fluorobenzyl)piperazineHCID 19689423N-benzyloxycarbonyl-3-(2,3-epoxypropyloxy)-4-methoxybenzylamine

Product 1

HCID 70069938N-Benzyloxycarbonyl-3-[{4-(4-fluorobenzyl)-piperazin-1-yl}-beta-hydroxypropyloxy]-4-methoxybenzylamineYield 69.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture comprising 2.4 g of N-benzyloxycarbonyl-3-(2,3-epoxypropyloxy)-4-methoxybenzylamine, 30 ml of ethanol and 1.4 g of 4-fluorobenzyl-piperazine, was refluxed under heating with stirring overnight. The mixture was cooled to room temperature, and then the reaction solution was concentrated under reduced pressure and extracted with chloroform. The organic layer was washed with an aqueous potassium carbonate solution and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol=19:1) to obtain 2.6 g of the above-identified compound.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with an aqueous potassium carbonate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThen, the solvent was distilled off under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol=19:1)

Sources & evidence

ORD record
ord-0947314ccd324486a49c9d07ce29c18d
Source dataset
uspto-grants-1999_07
Patent number
US05929074

Reaction notes

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