Benzaldehyde → HCID 59846084, compound

HRID 549924Notes

Reaction equation

HRID 549924 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([CH:19]3[CH2:24][NH:23][CH2:22][CH2:21][NH:20]3)=[O:18])[CH2:13][CH2:12]2)[CH:7]=[CH:8][C:9]=1[Cl:10].C(N(CC)C(C)C)(C)C.[CH:34](=O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:34]([N:23]1[CH2:22][CH2:21][NH:20][CH:19]([C:17]([N:14]2[CH2:13][CH2:12][N:11]([C:6]3[CH:7]=[CH:8][C:9]([Cl:10])=[C:4]([Cl:3])[CH:5]=3)[CH2:16][CH2:15]2)=[O:18])[CH2:24]1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 67158369HCID 67158369, compound

Product 1

HCID 59846084HCID 59846084, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(3,4-dichlorophenyl)-4-(piperazin-2-ylcarbonyl)piperazine dihydrochloride (150 mg), N,N-di-iso-propylethylamine (0.189 mL) and dichloromethane (10 ml) was stirred at room temperature under argon. After 5 minutes benzaldehyde (0.04 ml) was added followed by sodium triacetoxyborohydride (153 mg). The mixture was stirred overnight at room temperature and then filtered through a SCX-2 column eluting with methanol and then a 7M solution NH3 in methanol. The basic fraction was concentrated at reduced pressure. The residue was purified using reverse phase HPLC eluting with a mixture of 5-95% acetonitrile in water and then was filtered through a SCX-2 column eluting with methanol and then a 7M solution NH3 in methanol. The basic fraction was concentrated at reduced pressure. This gave 1-benzyl-3-{[4-(3,4-dichlorophenyl)piperazin-1-yl]carbonyl}piperazine as a colourless gum (125 mg).

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. filtrationfiltered through a SCX-2 column
  3. washeluting with methanol
  4. concentrationThe basic fraction was concentrated at reduced pressure
  5. customThe residue was purified
  6. washeluting with a mixture of 5-95% acetonitrile in water
  7. filtrationwas filtered through a SCX-2 column
  8. washeluting with methanol
  9. concentrationThe basic fraction was concentrated at reduced pressure

Sources & evidence

ORD record
ord-658689d2dc1e489aa0a9b0efee82175d
Source dataset
uspto-grants-2011_05
Patent number
US07943768B2

Reaction notes

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