1-Phenylpiperazine → HCID 20728545, compound

HRID 1583043Notes

Reaction equation

HRID 1583043 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS(O[CH2:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH:22]=[O:23])(=O)=O>CN(C)C=O>[C:29]1([CH2:28][O:27][C:26]2[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][C:19]=2[CH2:18][N:10]2[CH2:11][CH2:12][N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:8][CH2:9]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 70961-PhenylpiperazineHCID 21957468[2-(Benzyloxy)-5-formylphenyl]methyl methanesulfonate

Product 1

HCID 20728545HCID 20728545, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-phenylpiperazine (200 mg) and diiosopropylethylamine (130 mg) in dimethylformamide (1 ml) was added 3-[[(methylsulfonyl)oxy]methyl]-4-phenylmethoxybenzaldehyde (320 mg). After stirring at room temperature for 3 hours the reaction mixture was partially concentrated under reduced pressure and the residue was purified by flash chromatography column using petroleum ether:diethyl ether (1:3) as eluant. The pure fractions were combined and evaporated under reduced pressure to give a gum which was crystallized from diethyl ether to give 4-phenylmethoxy-3-[[(4-phenyl)-1-piperazinyl]methyl]benzaldehyde (320 mg) as white crystals. 1H NMR (CDCl3) δ9.95 (s, 1H, CHO); 5.23 (s, 2H); 3.80 (s, 2H); 3.30 (m, 4H); 2.78 (m, 4H). TLC (silica gel): Rf=0.7 (petroleum ether:diethyl ether, 1:4).

Workup

  1. concentrationwas partially concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography column
  3. customevaporated under reduced pressure
  4. customto give a gum which
  5. customwas crystallized from diethyl ether

Sources & evidence

ORD record
ord-81ea77d264bd49e7a08179af60532a5f
Source dataset
uspto-grants-2004_05
Patent number
US06740670B2

Reaction notes

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