1-(2-Methoxyphenyl)piperazine → 4-[4-(2-Methoxyphenyl)piperazin-1-yl]-1,2-diphenylbutan-1-one

HRID 1978877Notes

Reaction equation

HRID 1978877 reaction equation
[C:1]([CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:10][CH:11]=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.[Na].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]1[CH2:32][CH2:31][N:30]([CH2:11][CH2:10][CH:9]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 5360545SodiumHCID 12018120HCID 12018120, compound

Product 1

HCID 155240254-[4-(2-Methoxyphenyl)piperazin-1-yl]-1,2-diphenylbutan-1-oneYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 3-benzoyl-3-phenylpropionaldehyde residue obtained from Step B, above, (˜8.85 mmol) was dissolved in 110 mL of methylene chloride. To this solution was added 2-methoxyphenylpiperazine (10.61 mmol) and sodium triacetoxyboranehydride, NaBH(OAc)3, (10.61 mmol). The mixture was stirred at room temperature for 3 hours. Aqueous workup followed by flash chromatography gave pure product 1-(2-methoxyphenyl)-4-[3-(benzoyl)-3-(phenyl)propyl]piperazine (3.48 g) in 95% yield for last two steps. One equivalent of oxalic acid was added to the free base dissolved in methanol. The solvent was evaporated and the product was dried under vacuum to form the oxalate salt.

Sources & evidence

ORD record
ord-29ff3337f9914b088319e39d5c2942c8
Source dataset
uspto-grants-2001_05
Patent number
US06239135B1

Reaction notes

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