2-Pentanone → HCID 20735178, compound

HRID 1011263Notes

Reaction equation

HRID 1011263 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:30][C:31](=O)[CH2:32][CH2:33][CH3:34].C([O-])(O)=O.[Na+]>C(Cl)Cl.[Cl-].[Na+].O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH:32]([CH2:33][CH3:34])[CH2:31][CH3:30])[CH2:12][CH2:11]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 78952-PentanoneHCID 804471-(4-Nitrophenyl)piperazineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 20735178HCID 20735178, compoundYield 16.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A suspension of 1-(4-nitrophenyl)piperazine (5.00 g, 24.1 mmol, 1.0 eq), sodium triacetoxyborohydride (10.23 g, 48.3 mmol, 2 eq), and pentanone (6.23 g, 72.4 mmol, 3 eq) was stirred at RT in DCM (100 mL). Due to the viscous nature of the reaction mixture a further 50 mL of DCM was added to the reaction mixture (25 mL portion added after ca. 1 h; 25 mL portion added after 4 h). After 6 d, saturated aqueous NaHCO3 solution (25 mL) and 10% aqueous brine solution (25 mL) were added to the reaction mixture. The resulting mixture was stirred for 20 min, the phases separated, and the DCM extract washed with saturated aqueous NaHCO3 solution (25 mL), and 0% aqueous brine solution (25 mL) (50 mL total of aqueous soln in one wash). The phases were separated and the DCM extract dried by passing through a short column of MgSO4. The MgSO4 was rinsed with two portions of DCM (25 mL), and the combined DCM extracts evaporated on a rotary evaporator. To the residue obtained was added hexanes (25 mL) and the slurry stirred at rt for 24 h. The yellow precipitate which formed was collected by filtration and washed with hexanes (2×25 mL). On standing the required product precipitated from the filtrate. The precipitate was collected by filtration and dried under vacuum to provide the title compound as a yellow solid (1.13 g, 16% recovery, 87% purity as determined by LC/MS analysis @ UV 254 nm detection). The crude product was used in the next step without further purification. LCMS-ESI (m/z): calcd for C15H23N3O2, 277; [M+H]+ found, 278.

Workup

  1. customthe phases separated
  2. extractionthe DCM extract
  3. washwashed with saturated aqueous NaHCO3 solution (25 mL), and 0% aqueous brine solution (25 mL) (50 mL total of aqueous soln in one wash)
  4. customThe phases were separated
  5. extractionthe DCM extract
  6. customdried
  7. washThe MgSO4 was rinsed with two portions of DCM (25 mL)
  8. customthe combined DCM extracts evaporated on a rotary evaporator
  9. customTo the residue obtained
  10. stirringthe slurry stirred at rt for 24 h
  11. customThe yellow precipitate which formed
  12. filtrationwas collected by filtration
  13. washwashed with hexanes (2×25 mL)
  14. customprecipitated from the filtrate
  15. filtrationThe precipitate was collected by filtration
  16. customdried under vacuum

Sources & evidence

ORD record
ord-64683a554e924cc29dc8b180572deccc
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

Loading…